iii Tetrahedron: Asymmetry Vol. 24, No. 7, 2013 Contents REPORT Organocatalytic asymmetric synthesis of 3-amino-2-oxindole derivatives bearing a tetra-substituted stereocenter pp 343–356 Pankaj Chauhan, Swapandeep Singh Chimni* N N O R PG NuH N ∗ NH O R PG Nu N O R R' N X R'' N O R NCS R ' X N ∗ O R ∗ X NH S R' X = NR'' or O X = O, CHR'' N ∗ N O R HX R' R'' Chiral Organocatalysts ARTICLES Research on the pig liver esterase (PLE)-catalyzed kinetic resolution of half-esters derived from prochiral diesters pp 357–361 Naoyoshi Noguchi, Kazuhiro Tsuna, Masahisa Nakada* 0% ee PLE, KPB8, 10% acetone 30 °C, 7 d slow addition of half-ester over three days 47% recovery, 98% ee MeO 2 C CO 2 H Ph H MeO 2 C CO 2 H Ph H Enantioselective synthesis of orthogonally protected (2R,3R)-())-epicatechin derivatives, key intermediates in the de novo chemical synthesis of ())-epicatechin glucuronides and sulfates pp 362–373 Mingbao Zhang*, G. Erik Jagdmann Jr., Michael Van Zandt, Paul Beckett, Hagen Schroeter O OH OR 5 R 7 O OR 4' OR 3' OH R 7 O O OR 5 + OHC OR 4' OR 3' 10 steps 1a-j R R R R 1a MOM Bn Bn Bn 1b Bn PMB Bn Bn 1c Bn Bn MOM Bn 1d Bn Bn Bn MOM 1e Me MOM Bn Bn 1f Me Bn MOM Bn 1g Me Bn Bn MOM 1h MOM Me Bn Bn 1i Bn Me MOM Bn 1j Bn Me Bn MOM Contents lists available at SciVerse ScienceDirect Tetrahedron: Asymmetry journal homepage: www.elsevier.com/locate/tetasy
Transcript
iii
Tetrahedron: Asymmetry Vol. 24, No. 7, 2013
Contents
REPORT
Organocatalytic asymmetric synthesis of 3-amino-2-oxindole derivatives bearing a tetra-substituted stereocenter pp 343–356
Pankaj Chauhan, Swapandeep Singh Chimni*
N
N
O
R
PG
NuH
N
∗NH
O
R
PGNu
NO
R
R'
N
X
R''
NO
R
NCSR'
X
N
∗
O
R
∗X
NH
S
R'
X = NR'' or O
X = O, CHR''
N
∗N
O
R
HXR'R''
Chiral Organocatalysts
ARTICLES
Research on the pig liver esterase (PLE)-catalyzed kinetic resolution of half-esters derived from prochiral diesters pp 357–361
Enantioselective synthesis of orthogonally protected (2R,3R)-())-epicatechin derivatives, key intermediates in thede novo chemical synthesis of ())-epicatechin glucuronides and sulfates
pp 362–373
Mingbao Zhang*, G. Erik Jagdmann Jr., Michael Van Zandt, Paul Beckett, Hagen Schroeter
O
OH
OR5
R7O
OR4'
OR3'OHR7O
OOR5
+
OHC
OR4'
OR3'
10 steps
1a-j
R3´ R4´ R5 R7
1a MOM Bn Bn Bn1b Bn PMB Bn Bn1c Bn Bn MOM Bn1d Bn Bn Bn MOM1e Me MOM Bn Bn1f Me Bn MOM Bn1g Me Bn Bn MOM1h MOM Me Bn Bn1i Bn Me MOM Bn1j Bn Me Bn MOM
Contents lists available at SciVerse ScienceDirect
Asymmetric synthesis of an enantiomerically pure rivastigmine intermediate using ketoreductase pp 374–379
Madhuresh K. Sethi*, Somashekar R. Bhandya*, Nagaraj Maddur, Rohit Shukla, Anish Kumar, V.S.N. Jayalakshmi Mittapalli
O
ON
O
OH
ON
O
ketone (S)-alcohol
ketoreductase
NAD(P)H + H+ NAD(P)
glucosedehydrogenase
gluconic acid D-glucose
Highly diastereo- and enantioselective direct aldol reaction under solvent-free conditions pp 380–388
Furen Zhang, Chunmei Li, Chenze Qi*
R1 H
OO
R2 R3
Catalyst (5 mol%)
TFA (7.5 mol%), rtR1
R3R2
OH O
NH
NH
O
NH
N
O
SO O
up to >99:1 drup to >99% ee
Catalyst
Kluyveromyces marxianus CBS 6556 growing cells as a new biocatalyst in the asymmetric reduction of substitutedacetophenones
pp 389–394
Paola Vitale*, Cinzia D�Introno, Filippo Maria Perna, Maria Grazia Perrone, Antonio Scilimati
Kluyveromyces marxianusCBS 6556
CH3
O
growing cells
12 examplesee up to 96%
OH(S)
CH3H
R1
R2R3
R1
R2R3
Synthesis of enantiopure b2-homoalanine derivatives via rhodium catalyzed asymmetric hydrogenation pp 395–401
Susan Lühr*, Jens Holz, Odalys Zayas, Oliver Seidelmann, Lutz Domke, Armin Börner*
H2C CO2R1
N
H3C CO2R1
N
[Rh(PP)(COD)]BF4, H2
R2
R3
R2
R3
up to 99%ee
H3C
NH2
OH
PP =
catASium® MQF(R)
PP
FF
FF
iv
Asymmetric synthesis of multicyclic spiro-1,3-indandiones via a cascade Michael/Michael reaction of curcumins and 2-arylidene-1,3-indandiones
pp 402–408
Nian-hua Luo, Xiang Sun, Wen-tao Wei, Xue-jing Zhang*, Ming Yan
O
O
R1
R2
R1O
O
O
OHquinine (10mol%)
toluene
rt
R2
R2
O O
R2
13 examplesup to 97% yield;93% ee; 99:1 dr
Development of P*-monodentate diamidophosphites with a C1-symmetric 1,2-diamine backbone: the effects ofsubstituents in the 1,3,2-diazaphospholidine cycle on Pd-catalyzed asymmetric allylations
pp 409–417
Konstantin N. Gavrilov*, Alexei A. Shiryaev, Sergey V. Zheglov, Oksana V. Potapova, Ilya V. Chuchelkin, Ivan M. Novikov,Eugenie A. Rastorguev, Vadim A. Davankov
Ph Ph
X Nu
Ph Ph
Nu
up to 93% ee
*
OPN
NR Ph
OPN
NR Ph
R = Bn, sec-Bu,tert-Bu, i-Pr, Ph R = Bn, sec-Bu
Asymmetric hydrosilylation of cyclohexa-1,3-diene with trichlorosilane by palladium catalysts coordinated with chiralphosphoramidite ligands
pp 418–420
Hoon Seo Park, Jin Wook Han*, Ryo Shintani, Tamio Hayashi
+ HSiCl3Pd/L*
Cl3SiP N
Ph
PhPh
Ph
O
O
Aziridine ring-containing chiral ligands as highly efficient catalysts in asymmetric synthesis pp 421–425
Michał Rachwalski*, Szymon Jarzynski, Stanisław Lesniak
Ph +catalyst, Et2Zn
THFPh
OH
R
catalyst, Et2Zn
toluene R
OH
R H
O
R H
O
yields: 76-95%ee`s: 80-96%
catalysts:
N
OH
R2R1
N
OH
R2R1
aziridines:
N
H
Me
H N
H
Pri
H N
H
H
Pri
v
OTHER CONTENTS
Stereochemistry abstracts pp A75–A93
Tetrahedron: Asymmetry Reports pp I–IV
Cumulative author index pp V–VI
*Corresponding author
Available online at www.sciencedirect.com
Indexed/Abstracted in: Beilstein, BIOSIS Previews, Chemical Abstracts, Current Contents: Physical, Chemical and EarthSciences, Derwent Biotechnology Abstracts, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, PASCAL, ResearchAlert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus®. Full text availableon SciVerse ScienceDirect®
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