iii Tetrahedron: Asymmetry Vol. 24, No. 1, 2013 Contents ARTICLES Theoretical study of the imidazolidinone catalyzed 1,4-addition of N,N-dimethyl-3-anisidine with a,b-unsaturated butyric aldehyde pp 1–6 Zhang Lili, Zhou Zhongjun, Jiang Haiyang, Liu Huiling*, Huang Xuri N N + O Ph OCH3 N(CH3)2 iminium ion + R2 + Cl - + 2H2O OCH3 O (H3C)2N CH3 N N H O Ph ·HCl + +H2O P + catalyst + Thiourea-catalyzed asymmetric conjugate addition of a-substituted cyanoacetates to maleimides pp 7–13 Zhi-wei Ma, Ya Wu, Bin Sun, Hai-long Du, Wei-min Shi, Jing-chao Tao* COOEt H N S HN N 1a Cat. 1a (10 mol%) toluene, -30 o C 17 examples up to 97% yield 98/2 dr, 93% ee CN R 1 O O R 1 O O CN N N O O O O R 3 R 3 2 3 4 R 2 R 2 Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands pp 14–22 A. Ebru Aydin*, Seda Yuksekdanaci O H O 2 N + MeNO 2 OH O 2 N NO 2 6a ligand (10 mol %) Cu(OTf) 2 i PrOH, 0 o C 5 80% yield, 84% ee N N O H N O OH (4S,5R)-3a (4S,5R)-4a Contents lists available at SciVerse ScienceDirect Tetrahedron: Asymmetry journal homepage: www.elsevier.com/locate/tetasy
Transcript
iii
Tetrahedron: Asymmetry Vol. 24, No. 1, 2013
Contents
ARTICLES
Theoretical study of the imidazolidinone catalyzed 1,4-addition of N,N-dimethyl-3-anisidine with a,b-unsaturatedbutyric aldehyde
pp 1–6
Zhang Lili, Zhou Zhongjun, Jiang Haiyang, Liu Huiling*, Huang Xuri
N
N+
O
Ph
OCH3
N(CH3)2
iminium ion + R2
+ Cl-
+ 2H2OOCH3
O
(H3C)2N
CH3
N
NH
O
Ph
·HCl+ + H2O
P + catalyst
+
Thiourea-catalyzed asymmetric conjugate addition of a-substituted cyanoacetates to maleimides pp 7–13
Zhi-wei Ma, Ya Wu, Bin Sun, Hai-long Du, Wei-min Shi, Jing-chao Tao*
COOEt
HN S
HN
N1a
Cat. 1a (10 mol%)
toluene, -30 oC
17 examplesup to 97% yield98/2 dr, 93% ee
CNR1O
O
R1O
O
CNN
N
O
O
O
O
R3
R3
2 34
R2 R2
Asymmetric Henry reactions catalyzed by metal complexes of chiral oxazoline based ligands pp 14–22
A. Ebru Aydin*, Seda Yuksekdanaci
O
H
O2N+ MeNO2
OH
O2N
NO2
6a
ligand (10 mol %)Cu(OTf)2
iPrOH, 0 oC
5 80% yield, 84% ee
NN
O
H N
O
OH
(4S,5R)-3a (4S,5R)-4a
Contents lists available at SciVerse ScienceDirect
Lewis acid mediated asymmetric Diels–Alder reactions of chiral 2-phosphonoacrylates pp 23–36
Jia-Liang Zhu*, Po-Erh Chen, Hue-Wen Huang
R*OP(OEt)2
O OSnCl4 (1.2 equiv),
CH2Cl2, -65 oC
R* =
PO(OEt)2
> 99:1 endodr's 50:50 to > 99:181-89% yield
CO2R*
R
R = Ph, H
Ph
R
R(10 equiv)
Enzymatic preparation of (1S,2R)- and (1R,2S)-stereoisomers of 2-halocycloalkanols pp 37–42
Olga O. Kolodiazhna, Anastasy O. Kolodiazhna, Oleg I. Kolodiazhnyi*
OH
X
(CH2)n
OH
X
(CH2)n
(1S,2R)- (1R,2S)-
n=1,2; X = Cl, Br, I
Systematic evaluation of a few proline derivatives as catalysts for a direct aldol reaction pp 43–49
Revannath L. Sutar, Navalkishore N. Joshi*
NH
X
XH
H
H
NH XH
R
Y
NH XH
H
Y
X = N, Y = CORR = H, Me, BnX = N, O
O
+Ar
O
H
O
Ar
catalyst*
solvent, rt
OH
*
catalyst* =
Ar = 4-NO2Ph
Two optimized synthetic pathways toward a chiral precursor of Mivacurium chloride and other skeletal musclerelaxants
pp 50–55
Beáta Vilhanová, Václav Matoušek, Jirí Václavík, Kamila Syslová, Jan Prech, Jan Pechácek, Petr Šot, Jakub Janušcák,Jaromír Toman, Jakub Zápal, Marek Kuzma, Petr Kacer*
N
R
MeO
MeON
R
MeO
MeO N
R
MeO
MeO
A B
1. ATH2. methylation
1. (–)-DBTA2. crystallization
R = 3',4',5'-trimethoxybenzyl
(–)-DBTA = (–)-2, 3-dibenzoyl-L-tartaric acid
(R)-5'-methoxylaudanosine
Mivacurium chloride
iv
Remote regio- and stereocontrol by the sulfinyl group: Diels–Alder reaction of sulfinyl dienols and8,8-dimethylnaphthalene-1,4,5(8H)-trione
pp 56–61
Iriux Almodovar*, Wilson Cardona, Tomás Delgado-Castro, Gerald Zapata-Torres, Marcos Caroli Rezende,Ramiro Araya-Maturana*, M. Carmen Maestro, José L. García Ruano
OO
O
3
HO
S
1: (2S,SR)
2: (2R,SR)
pTolO
i. C6H6
ii.SiO2
OOH
OH
HO
S
OOH
OHHO
S
+*
*
*
*
*
yield = 80-70%
regioselectivity = 80%
π-facial selectivity = 90-95%
*
O pTol
pTol
O
+
*
Synthesis and enantiomeric recognition studies of a novel 5,5-dioxophenothiazine-1,9 bis(thiourea) containingglucopyranosyl groups
pp 62–65
Attila Kormos, Ildikó Móczár, Dávid Pál, Péter Baranyai, József Kupai, Klára Tóth, Péter Huszthy*
Fine tuning of the structure of phosphine–phosphoramidites: application for rhodium-catalyzed asymmetrichydrogenations
pp 66–74
Szabolcs Balogh, Gergely Farkas, Áron Szöll}osy, Ferenc Darvas, László Ürge, József Bakos*
O
OP N
PPh2
O
OP N
PPh2
O
OP N
PPh2
O
OP N
PPh2
(S)-(2S,4S)-1 (S)-(2R,4R)-2 (S)-(2S,4S)-4(S)-2
Stereoselective cyclopropanation of chiral 5-substituted dihydro-2H-piperazines pp 75–79
Gianna Reginato*, Maria Pia Catalani, Alessandro Mordini, Bernardo Pezzati, Andrea Bernardelli, Silvia Davalli, Nicola Pace
N
N
R
Bn
BocN
N
R
Bn
Boc
ZnEt2CH2I2
50-80%
single diastereoisomer
v
OTHER CONTENTS
Stereochemistry abstracts pp A1–A15
Cumulative author index p I
*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®
