Facile stereoselective syntheses of (E)- and (Z)-α-substituted cinnamates by stereoselective dehydration reaction with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)

被引：17

作者：

Sai, H ^{[1
]}

Ohmizu, H ^{[1
]}

机构：

[1] Tanabe Seiyaku Co Ltd, Discovery Res Lab, Osaka 5328505, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(99)00923-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly stereoselective syntheses of (E)- and (Z)-alpha-substituted cinnamates have been achieved by dehydration reaction of anti- and syn-alpha-substituted-beta-hydroxyphenylpropionates with EDC in good yields. This facile method has been applied to the stereoselective syntheses of (E)- and (Z)-alpha-alkylidene-gamma-butyrolactones. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5019 / 5022

页数：4

共 9 条

[1] Z-selective Horner-Wadsworth-Emmons reaction of α-substituted ethyl (diarylphosphono)acetates with aldehydes
Ando, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8411 - 8416
[2] ENANTIOSELECTIVE TOTAL SYNTHESIS OF GRACILIN-B AND GRACILIN-C USING CATALYTIC ASYMMETRIC DIELS-ALDER METHODOLOGY
COREY, EJ
LETAVIC, MA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) : 9616 - 9617
[3] NUCLEOSIDIC ENOL ESTERS - A VERSATILE TOOL FOR THE SYNTHESIS OF 3'-CARBON-SUBSTITUTED NUCLEOSIDES
HARAGUCHI, K
TANAKA, H
ITOH, Y
MIYASAKA, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (06) : 777 - 780
[4] PREPARATION OF BETA-HYDROXY-ALPHA-PHENYLTHIO ESTERS VIA CONDENSATION OF ALDEHYDES WITH ALPHA-PHENYLTHIO ESTER ENOLATE ANIONS
HOYE, TR
KURTH, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (18) : 3549 - 3554
[5] KAUREN J, 1987, ANGEW CHEM INT ED EV, V26, P773
[6] SIMPLE SYNTHESIS OF ALPHA-YLIDENE GAMMA-LACTONES FROM GAMMA-TRIMETHYLSILOXY NITRILES
MATSUDA, I
MURATA, S
IZUMI, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (08) : 2389 - 2393
[7] Ohtani A, 1996, J BIOCHEM-TOKYO, V120, P1203
[8] A STEREOSELECTIVE SYNTHESIS OF (Z)-ALPHA,BETA-DISUBSTITUTED ACRYLATES
SHIMAGAKI, M
SHIOKAWA, M
SUGAI, K
TERANAKA, T
NAKATA, T
OISHI, T
[J]. TETRAHEDRON LETTERS, 1988, 29 (06) : 659 - 662
[9] DIRECT SYNTHESIS OF Z-UNSATURATED ESTERS - A USEFUL MODIFICATION OF THE HORNER-EMMONS OLEFINATION
STILL, WC
GENNARI, C
[J]. TETRAHEDRON LETTERS, 1983, 24 (41) : 4405 - 4408

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