Subject Index
Note: page numbers in italic refer to schemes.
2-acetal-4-butanolide, hydrogenationof 53
a-acetamido-b-ketoesters 50, 51a-acetoxy-d-butyrolactone, reductionof 146, 147
acetylcyanation 132, 134, 135acetylmandelic acid esters 1936-acetyloxy-2H-pyran-3-one 153,154
N-acylaminonitriles 169N-acylhemiaminals
DKR with amides 18–19DKR with lipases 154, 156
acyloins 158–9, 161tricyclic 152, 153
5-acyloxy-2-furanones 154, 1555-(acyloxy)pyrrolinones 154, 155aflatoxins B1 and B2 87, 89Agrobacerium radiobacter 179Alcalases 169alcohol dehydrogenase 149, 151–2alcohols
enzyme–iridium DKR 225, 227enzyme–rhodium DKR 225enzyme–ruthenium DKR
acylation conditions for (R) and(S)-esters 236
Backvall’s catalyst 196–8, 199,200, 211–12diarylethanols 213, 215diols 205–6, 207, 212, 214fluorinated aryl alcohols 197,200
novel aminocyclopentadienylcatalyst 195, 198
novel dinuclear catalyst 201,203
polymer bound catalyst 197–8,201
Shvo’s catalyst 192–6, 200, 202,206, 208, 219–20, 221heteroaryl substitutedethanols 216–17, 219
enzyme–vanadium DKRallenic alcohols 226, 228benzylic alcohols 227–8
enzyme–zeolite DKR 161–3,164–5, 228–9
isomerisation of allylic alcohols 84synthesis
allylic alcohols 91b-amido alcohols 70, 72b-aryloxy alcohols 74–5, 77, 78dialkylamino alcohols 72–6fluorinated alcohols 61–22-sulfonyl alcohols 78, 80via enzymatic reduction 146
aldehydescycloaddition withcyclopropane 110, 112
DKR of b-branchedaldehydes 228
DYKATs of b-hydroxy 120–1enzymatic reduction 147, 148,151–2
hydrogenation 76, 78–80
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aldehydes (continued)lactone concept/biaryl hydroxyaldehydes 255–6, 257
reductive amination 122, 126aldol reaction, intermolecular 121–2alkaloids 268, 270,272
see also cinchona3-alkoxy-4-hydroxy-butenes 90alkyl halides, configurationallylabile 1–14
b-alkylamino alcohols 73–4, 75, 762-alkyl-3-hydroxyketones 64–5a-alkyl-b-ketoesters, reductionof 148, 150
a-alkylidene-b-hydroxy esters 106alkylpiperidines 22allenes
chemoenzymatic DKR 226–7, 228DYKATs of 91, 93
allenic alcohols 226, 228allenic esters 84–5allylic acetates
DYKATs of 91, 92palladium–enzyme DKR 235, 236
allylic alcoholsShvo’s catalyst DKR 193, 195synthesis 91vanadium–lipase DKR 225, 226
allylic alkylation 103, 109, 110allylic carbonates, DYKATs of 91,92
allylic thioesters, DYKATs of 90, 91aluminium–enzymatic DKR 225, 227b-amide alcohols 70, 72a-amide ketones, hydrogenationof 70, 72
(S)amides 175–7, 176(R)amides 174–5, 176a-amido-b-ketophosphonates,hydrogenation of 71, 73
a-amidopropiophenones,hydrogenation of 66–7
aminesenzyme–metal DKR
iridium catalyst 232, 234nickel catalyst 234
palladium catalyst 222,229–34
Shvo’s Ru catalyst andanalogues 222–4
as nucleophiles 2–3, 4, 6, 12, 13oxidation 183Pd/microwave promotedDKR 230–1
selenium-containing 231–2transesterification/hydrolysis173–7
see also diaminesamino acid
a-aryl 115, 116b-amino 2enantiopure 153, 154, 168–9general derivatives 3, 12, 16,17, 87
racemisation with zinc catalyst235
amino acid amides, hydrolysis of 169,170
amino acid esters 33–4, 35, 40, 42hydrolysis 169, 170racemisation with catalyticaldehydes 172–3
Schiff bases of 166amino acid thioesters 117, 118amino alcohols
aromatic 1,2-amino 183b-amino 29, 31, 34, 35
hydrochlorides 97, 100a-amino aldehydes 28, 30a-amino-b-ester hydrochlorides,hydrogenation of 107, 108, 109
a-amino-b-hydroxyesters 58amino imides 2a-amino-b-ketoesters, hydrogenationof 55–62hydrochlorides 59–61, 96–7, 99
a-amino ketones, hydrogenationof 72–5hydrochlorides 97, 100
a-amino nitriles 181–22-amino-4-phenylbutanoic acid 167,168
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amino phosphines 388-amino-5,6,7,8-tetrahydroquinoline174, 175
Amycolatopsis orientalis 168anions, configurationally labile 14–16aryl alcohols, fluorinated 197, 200a-aryl aldehydes 76, 78, 80a-aryl amino acids 115, 1165-aryl-1,3-dioxalane-2,4-diones 115aryl–ferrocenyl ligands 272, 2762-aryl propionaldehydes, reductionof 151, 152
aryl proponic acids 8–9, 17, 18b-aryloxy alcohols 74, 74–5, 77a-aryloxy propanoic acidherbicides 3, 7
asparagine 180–1atropisomeric amides 120, 121
benzamides 257–8naphthamides 257–8
atroposelective reactionsbackground and summary 243–4,276–8lactone concept 245–6
bridge cleavage (atroposelective)biaryl hydroxyaldehydes 254–5, 257
biaryl lactones 245–54, 255,256, 257
non-biaryl atroposomers 255–8bridge formation(atroposelective) 260–6
DKR via bridgedintermediate 266–7
DKR via o-substituents 258–60, 261synthesis of
axially chiral reagents 271–7natural products 268–71
aza-Cope rearrangements 43, 442-azetidinone, fluorinated 61a-azido/aminocarboxylic acidderivatives 8
b-azidoacetates 192, 193aziridines
vinyl 93zircon-derivative 33, 35, 40, 42
azlactonesorganocatalysed DKR 115, 116,117–19
ring opening 154, 156
Backvall’s catalyst 196–8, 200, 216chlorohydrins 211–12diarylethanols 213, 215diols 205–6, 207, 212, 214fluorinated aryl alcohols 197, 200
Bacillus caldolyticus 167Bacillus kaustophilus 167baclofen 109Baeyer–Villigermonooxygenases 177–9
bafilomycin A 64–5baker’s yeast 145–6, 147balanol 56–7barium-catalysed reactions 106–7Baylis–Hillman adducts, DYKATsof 90
benanomicin B 271, 274benzazepines 642-benzenesulfonylcyclohexanones,reduction of 147
benzhydryl quinuclidinone 124, 127benzoins, DKR of 204, 205, 216, 219benzo[a]quinolizidines 23, 25benzotetramizole catalyst 118, 119a-benzylamino-b,g-unsaturatedacids 9, 10
benzyl carbamates 223benzyl ketones 177, 178benzylic alcohols 161, 162, 164–5
and Shvo’s catalyst 192, 193and vanadium catalyst 227–8
benzylic aminesPd/microwave promotedDKR 230–1
nickel–enzymatic DKR 2344-benzyloxazolidinone 166, 1672-benzyloxymethylcyclopentanone
177, 179benzyltrimethylammoniumhydroxides 164
biaryl amides 246, 247, 248, 249
291Subject Index
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biaryl biscarbazoles 269, 270, 271biaryl helicene quinones 25–6, 28,258, 260
biaryl hydroxy aldehydes 255–6, 257biaryl lactams 262, 263biaryl lactones 245–6
catalysed ring-opening 252–4, 255condensation of a lithiatedsulfoxide 248, 250
nucleophilic cleavagealcoholysis 246–7, 247, 248amidolysis 246, 247, 248, 249ring-opening with amino acidesters 248, 249
reduction 249, 250, 251, 253, 255biaryl thioethers 253–4, 256biaryl thiophenols 252, 253bicoumarins 268, 269, 270bidentate N-, O- ligands 271, 275bienzymatic DYKAT 183BINOL phosphoric acid catalyst 122,124, 126, 127
biocatalysts see enzymatic methodsbiphenomycin 542,20-bipyridine N,N0-dioxides 263,264
biscarbazoles 268, 270, 271bis(oxazolinyl)biphenylderivatives 265
bis-sulfinate esters 32–3boranes 15–16borohydride reduction 98–9, 101,102, 103, 253, 255
brefeldin A 87bromination,organocatalyzed 259–60, 261
a-bromoamides 9–10, 11a-bromocarboxylic acids 23-bromocyclohex-1-enes, alkylationof 103, 106
a-bromoesters 3, 4, 8–9, 12, 15hydrolysis of 165, 166
broussonetine G 86bulgecinine 86butadiene monoepoxide 85–7butanamides 174, 175
butanolides 532-(3-butenyl)azlactone 154, 156t-butyl 4-methyl-3,5-dioxohexanoate,reduction of 147, 148, 149, 151
caprolactoneschiral polymerisation of 210–11pentafluoro 28
2-carbethoxycycloheptanone,reduction of 146, 147
carbocyclic nucleosides 218, 220carbohydrate-mediated DKR11–114
carbonates 109, 111allylic 92diphenylethylene 33–4, 35, 40, 42
cascade reactions 35–6Michael/Michael/Wittig 131–2,133
catalysts see enzymatic methods;metal-catalysed; organocatalysed
chiral auxiliaries 1–45cycloadditions 24–7cyclocondensations 20–3esterification andtransesterificationreactions 16–20
nucleophilic substitutionon configurationally labile alkylhalides 1–14
on configurationally labileanions 14–16
reduction reactions 23–4synthesis of axially chiralagents 271–8
various miscellaneousreactions 27–44
chiral bridges 260–6chiral catalysts see metal-catalysed;organocatalysed
b-chloroacetates 211, 211a-chloro-b-hydroxyesters 53–4a-chloro-b-ketoesters, hydrogenationof 53
2-chloromandelic acid 168, 169chlorophoshines 126, 129
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2-chloroproprionate, aminolysisof 183
chromium-catalysed reactions 101,104
cinchona alkaloid-basedcatalysts 113, 115, 117, 118, 122,125, 129domino Michael reactions 129–30,131
clofibrate analogues 4, 5, 8cobalt-catalysed reactions 98–9, 101conduritol B 91copper-catalysed reactions 39, 101–3,105, 106de-racemisation of biaryls 265, 267Ullmann couplings 266–7
cyanocarbonation 122, 125cyanohydrins 154–7, 158, 159, 164,169hydrolysis 168, 169
cyclic ketonesaddition of HCN 179–80copper-catalysed DKR 101–2, 104hydrogenation of 66, 67, 68
2-arylated 66cyclohexanones 63, 76, 79a-haloketones 67–8
macrocyclic 39–40, 41cyclocondenstaion reactions 20–3, 241,3-cyclohexanediol 206, 207cyclohexanones, hydrogenationof 63, 76, 79
cyclopenadienyl benzoyl rutheniumcatalyst 213
cyclopentanones, addition of HCNto 179–80
cymene–ruthenium complexes 193,195, 198–201, 210, 220–1
diacetone-D-glucose chiralauxiliary 12, 13
3,5-dialkylcyclopentenones 101–2,104
diamines1,2-substituted 29, 31, 84, 85vicinal 84, 85, 87, 88
1,2-diaryl ethanols 213, 215diazonamide A 2612,20-dibenzoyl chloride 260, 262dibenzyl carbonate 223Diels–Alder/domino reaction 204–5,206
(R)-dihydrobenzoxalinones 12, 14(R)-dihydroquinoxalinones 12, 14diketones
enzymatic reduction 147, 148, 150hydrogenation of 64–5macrocyclic 40, 41
diltiazem 54intermediate 23, 26
diolsBackvall-catalysed DKR 205–6,207, 212, 214
monodichloroacetates 119, 120poymerisation of 206–7, 208
dipeptides 9, 10diphenylethylene carbonate 40, 42diphosphines 40, 43disulfide catalyst 126–7, 129dolaproine 54, 55, 55domino reactions
DKR/Diels-Alder 204–5, 206Michael reaction 129–30, 131
DYKAT reactions 85–95, 103, 106bienzymatic process 183b-hydroxyaldehydes 120–1organocatalytic 131–2
dynamic kinetic resolution, definitionof 283–4
enamine hydrosilation 127, 129, 130enamionones 32enol acetates 195, 197Enterococcus sp. 183enzymatic methods 145
hydrolysis andesterification 152–73
miscellaneous reactions 173–83reduction 145–52see also metal–enzyme reactions
epibromohydrin 179, 180epichlorhydrin 101, 104, 179
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esterification, enzymatic 152–73ethambutol 86ethyl 3-amino-3-phenylpropanoate 223
ethyl 2-fluoroacetoacetate 95–6ethyl 1,2,3,4-tetrahydoisoquinoline-1-carboxylates 172
eupomatilone-3 102–3, 105
fenoprofen 17, 18, 171fluorinated aryl alcohols 197, 200a-fluoro-b-hydroxy esters 96fluoro-g-valerolactone 28flurbiprofen 17, 182-formylarylamides 36, 3720-formylbiphenyl-2-carboxylicacid 262, 263
FR9000482 antitumor agent 87, 88furaquinocins 90furylbenzothiazole-basedcyanohydrins 154–6, 157
glucopyranose derivative 260, 262glycidates 54Grignard reagents 29, 31, 103, 106GW597599 antagonist 130gymnangiamide 62–3
a-haloacylimidazolidinones 4–7, 8b-haloalcohols, metal–enzymaticDKR 192, 194, 225–6, 227, 228
a-halocarboxylic acids 1–2a-haloesters 12, 13, 14, 15, 166, 166halohydrins 68Heck reaction, intramolecular 92, 94,263, 264, 265
hemithioacetals 152, 153Henry reaction 163hippospongic acid A 90hydantoin 167hydantoinase 167–8hydrazines, DYKAT of 871,2-hydrazino alcohols 96, 98a-hydrazino-b-ketoacids, reductionof 96, 98
hydrobenzoin 63, 64
hydrolysis, enzymatic 152–73hydroxy acids 3
d/g-derivatives 192, 194b-hydroxy aldehydes, DYKATsof 120–1
b-hydroxy amides 70, 71g-hydroxy amides 204, 205b-hydroxy-a-amino esters 96–7, 99,107, 108
a-hydroxy carboxic acid esters 192,193
2-hydroxy cyclohexanone, reductionof 149
5-hydroxy-d-decalactone 147, 148b-hydroxy esters 192, 194hydroxy ketones 64–53-hydroxy leucines 55–6, 57a-hydroxy malonates 97, 100hydroxy nitrile lyase 179–80b-hydroxy nitriles 192, 1932-hydroxy-4-phenylbutyric acid 168,169
a/b-hydroxy phosphonates 202, 204b-hydroxy sulfones 71, 74, 204, 205b-hydroxyalkyl sulfones 204, 205hydroxyalkylferrocenederivatives 220, 221
hydroxylamines, DYKAT of 873-hydroxylsyline 50, 52
ibuprofen 8–9, 17, 18, 169–71imidazolidinones 4–7, 8, 91, 93indolo[2,3-a-]quinolizidines 23, 25ionic liquids 163, 164, 201, 203, 210iridium-catalysed reactions 108–9iridium–enzymatic DKR
alcohols 225–6, 227, 228b-branched aldehydes 228secondary amines 232, 234
iron-catalysed reactions 101, 104isokotanin A 268, 269, 270isoprene monoperoxide 90isoschizandrin 270, 273
Kabachnik–Fields reaction 130, 132ketimines, hydrogenation of 81, 82
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b-keto aldehydes, reduction of 147,148
b-keto amides, hydrogenation of 68,69, 71
a-keto esters, aldol reaction 121–2,123
b-keto estersenzymatic reduction 148, 150hydrogenation 49–50, 51
a-substituted 54–62cyclic esters 50–2
3-keto esters, borohydridereduction 99, 103
a-keto ethers, hydrogenation of 95b-ketoiminocobalt complex 253, 255b-keto nitriles 148, 149b-keto phosphonates, hydrogenationof 71, 73
keto piperazine 131–2, 133keto reductases 148–9b-keto sulfones, hydrogenation of 71,74
b-keto sulfoxides, biaryl 248, 250ketones
borohydride reduction 98–9, 101,102
conversion to chiral acetates 195,197
enzymatic reduction of a,b-unsaturated 149, 150
hydrogenation of 63–8, 69, 74–5, 76synthesis of muscone 39–40, 41see also cyclic ketones; diketones
kinetic resolution, definition of 283Kloeckera magnus 146knipholone 268–9korupensamines A and B 270, 272
lactam bridge 262, 263lactamide chiral auxiliaries 8–9, 17, 18lactamisation 21–3, 24b-lactams 70, 149, 150lactone concept 244–5lairdinol A 40, 42lanthanum-catalysed reactions 110,113
leucine 166, 167ligands
spiral diphosphine 76SYNPHOS diphosphane 58synthesis of chiral 271, 272, 275,276
lipozyme 154lithiopyrollidine derivative 111, 114
M58163/58169 agents 110, 113macrolactonisation reaction 261,262
magnesium-catalysed reactions 110,112
malonic ester enolates 2mandelic acid derivatives 168, 169,193chiral auxiliaries 12, 14, 15
mandeonitrile acetate 157, 160Manihot esculenta 180mastigophorenes A and B 268, 269menthol 24, 27metal-catalysed DKR
barium 106–7chromium 101, 104cobalt 98, 101copper 101–3, 105, 106iridium 108–9iron 101, 104lanthanum 110, 113magnesium 110, 112molybdenum 109–10, 111nickel 96–7, 98, 99, 100palladium 84–5, 94–5
DYKAT transformations85–94
resolution of palladiumcomplex 94
platinum 95–6, 97rhodium 107ruthenium
alkylation of phosphines 82–4hydrogenation 49–82
titanium 111, 114see also metal–enzyme catalysed
DKR
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metal–enzyme catalysed DKR 191,236–7alcohols
aluminium–enzyme 225, 227iridium–enzyme 225–6, 227,228
palladium–enzyme 226–7, 228rhodium–enzyme 225ruthenium–enzyme 191–221vanadium–enzyme 225, 226,227–8
zeolite–enzyme 228–9allylic acetates 235–6amines 222–4, 229–35
N-methyl a-aminonitriles 182methyl 2,3-dihydro-1-indene-1-carboxylate 170, 172
methyl p-chloro-3-hydroxytyrosinate 50, 51
methyl (S)mandelate chiralauxiliary 12, 14, 15
Michael reactions, domino 129–30,131
Michael/Michael/Wittigcascade 131–2, 133
microwave promotion 230–1molybdenum-catalysedreactions 109–10, 111
monooxygenases 177–9Morita–Baylis–Hillman acetates 124,127
Mortierella isabellina 147muscenone 39–49muscone 39–40, 84
N-phthaloyl-L-alanine 2naphthylisoquinoline alkaloids 268,270, 272
2-(1-naphthyl)-3-methylpyridine 258,261
naproxen 171natural products, synthesisof 268–71, 272, 273, 274
neonicotinoide pesticide 211, 213nickel-catalysed reactions 96–7, 98,99, 100
nickel–enzymatic DKR 234b-nitroalkanols 163non-enzymatic catalysts see metal-catalysed; organocatalysed
noradrenaline 183Novozyme 154, 162, 163, 164
2-octanol 161octopamine 183organocatalysts 112–35oxazolidines 21–3oxazolidinones 19–20, 84oxazolones 154, 155
ring opening 162, 1632-oxo-3-aryl-succinates 122, 1242-oxocycloalkanecarbonitriles,reduction of 148, 149
2-oxocyclopentanecarboxamides,reduction of 147, 149
a-oxoesters 132, 134b-oxoesters 145–6oxoflavopiridols 34, 363-oxo-4-phenyl-b-lactam, reductionof 149, 150
palladium-catalysed reactions 84–95,222nanocatalyst 229–30, 232
palladium–enzymatic DKRalcohols 226–7, 228allylic acetates 235, 236amines 222, 229–34
(R)-pantolactones 3pentafluoro-g-caprolactone 28pentaphenylcyclopentadienylruthenium chloride 195, 198
peptide derivatives 9–11, 62–3phenolthiazine-basedcyanohydrins 156, 159
phenylalanine ethyl ester, hydrolysisof 169, 170
phenylanthraquinones 268–91-phenylethanol, DKR of 162–3
acid zeolite–enzyme 228–9Backvall’s catalyst 196–8, 200,213, 216
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cyclouthenated amine 207, 209indenyl ruthenium complex 192,194
ruthenium/TEMPO system 195–6ruthenium–cymene catalyst220–1
Shvo’s catalyst 192, 193treated subtilisin 209–10vanadium catalyst 228
1-phenylethyl acetamide 2295-(2-phenylethyl)-imidazolidine-2,4-dione 168
1-phenylethyl octanoate 228–91-phenylethyl proprionate 229phenylfuran-basedcyanohydrins 156, 158
phenylglycine derivatives 166, 167ammonolysis of ester 174DKR of amides 232, 233
2-phenyl-5-oxazolones 154, 1552-phenyl-propiophenone,hydrogenation of 63
a-phenylpyrrolidin-2-one 180, 181phosphination, Pd-catalysed 94, 95phosphine-boranes 15–16, 82, 83,112, 115
phosphinesalkylation of 81–2, 83, 96, 97synthesis of chiral ligand 271,275
phosphonates, chiral 28, 30a-phthalimidyl ketones,hydrogenation of 68, 69
(N)-phthalylaminoacids 16, 17pipecolic acid esters 174, 175piperidine derivatives 20–2platinum-catalysed reactions 95–6, 97polymers, chiral 210–11preclamol analogues 21–2profens 151proline
DKR of methyl esters 174, 175b-keto-a-methyl esters from 54, 55as organocatalyst 119–21, 122,123, 124, 132
Ru catalyst from 84
prolinol derivatives 10, 11, 29propargyl mesylates 38–9protein kinase C inhibitor 86Pseudomonas sp. 152, 154, 156, 158,163–4, 183
quinidine catalyst 126, 128
reduction reactionsborohydride 98–9, 101,102, 103
chiral auxiliaries 23–4enzymatic 145–52
reductive cross coupling 31rhodium-catalysed reactions 107rhodium–enzymatic DKR 225Rhodococcus sp. 151ribonucleoside phosphonatediesters 43
rivastigmine 211–12, 213Ro 67-8867 synthesis 70rotaxane-based molecular shuttle 42Rove beetle pheromone 27–8, 29roxaticin 54roxifiban 170ruthenium catalysts 50, 51
alkylation of phosphines 82–4configurationally labile 265–6hydrogenation 49–82polymer-immobilised catalyst 70Ru–BINAP catalyst 201, 203Ru–cyclopentadienyl catalyst216
Ru–cymene catalyst 193, 195,198–201, 210, 220–1
ruthenium–enzymatic DKRalcohols 191–221amines 223, 224
Saccharomyces cerevisiae 151Sch 39166 synthesis 64Schiff bases 165–6scyphostatin 180, 181selenium-containing amines 231–2sesquiterpenoid biphenyls 268,269
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Shvo’s catalysed DKR 192–5, 197,200, 202, 204, 205amines 222–4heteroaryl ethanols andbenzoin 216–17, 219
hydroxyalkylferrocenederivatives 220, 221
primary alcohols from tropic acidethyl ester 219–20, 221
synthesis of carbocyclicnucleoside 218, 220
b-silyloxy-a-ketoester, hydrogenationof 63
solenopsin 212, 214(–)-sparteine 14–15, 16spiral diphosphine ligands 76stagonolide-C 215–16, 217steganone 270–1, 274Strecker reactions 181–2substance P antagonists 124subtilisin 209–10, 236sulfinate esters 32–3, 124–5, 128sulfinyl chlorides 38, 124–6, 128sulfinyl diene complexes 37, 266sulfobacin A 58, 59sulfone derivatives 71, 74, 204, 2052-sulfonyl aldehydes, hydrogenationof 78, 80
suprofen 171SYNPHOS ligand 58synthase inhibitors 54
tandem metal–enzyme reactions seemetal-enzyme
tartaric acid catalyst 124, 127taxotere 54ternaphthyl bislactone 275, 276, 277tetrahydrofurans 110, 1121,2,3,4-tetrahydro-1-naphthylamine 223, 224
1-tetralones, hydrogenation of66, 67
tetramethoxybiphenyl-3, 30-diyldimethanethiol 158, 160
tetrapeptides 10, 11
thioamides 30, 32thiobiphenyls 158, 160thioesters
allylic 90, 91hydrolysis of 165transesterification of 152
thioflavopiridols 34, 36thiomide-based catalyst 119, 120thionolactone rutheniumcomplexes 253, 256
thiourea-based catalyst 115, 116tipranavir 109titanium-catalysed reactions 111,114
(tolylsulphinyl)benzylcopperreagent 39
transesterificationamines 173–7chiral auxiliary reactions 16–20intramolecular 19–20thioesters 152
transition metals see enzyme–metalcatalysis; metal-catalysed DKR
tricyclic acyloin 152, 153tricyclodecadienones 30, 32a-(trimethylsilyl)methyl-b-ketosufoxides 23, 26
tripeptides 10, 11tripodal ligands 272, 276tropic acid ethyl ester 219–20, 221
U-100592 antibacterial 101, 104Ullmann couplings 266–7urea-based catalysts 118
valine-derived formamidecatalyst 127, 129, 130
valinol 262, 263vanadium–enzymatic DKR 225,226allenic alcohols 226, 228benzylic alcohols 227–8
vancomycin 50, 270, 273vanol 267vapol 267
298 Subject Index
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vigabatrin 86vinyl aziridines, DYKAT of 93vinyl epoxides 87vinylglycerol 86viridenomycin, cyclopentyl coreof 88, 89, 90
Yarrowia lipolytica 146
zeolite–enzymatic DKR 161–3,164–5, 228–9
zinc catalyst 235zirconaaziridines 33, 35, 40, 42
299Subject Index
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nloa
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by M
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titut
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on 2
8 Fe
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013
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04
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i:10.
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Dow
nloa
ded
by M
assa
chus
etts
Ins
titut
e of
Tec
hnol
ogy
on 2
8 Fe
brua
ry 2
013
Publ
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d on
04
Apr
il 20
11 o
n ht
tp://
pubs
.rsc
.org
| do
i:10.
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/978
1849
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0289
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