A chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal from ethyl 1,3-dithiolane-2-carboxylate. Synthesis of acetate aldols in high enantiomeric purity

被引：31

作者：

Kiyooka, S

Hena, MA

机构：

[1] Department of Chemistry, Faculty of Science, Kochi University, Kochi 780, Akebono-cho

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 08期

关键词：

D O I：

10.1016/0957-4166(96)00265-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric synthesis of dithiolane aldols 3 was achieved in good yields by using silyl ketene acetal 1, derived from ethyl 1,3-dithiolane-2-carbylate, in the chiral oxazaborolidinone (L-l and D-2)-promoted aldol reaction and desulfurization of 3 resulted in production of acetate aldols 4 in high enantiomerc purity. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2181 / 2184

页数：4

共 3 条

[1] Highly enantioselective synthesis of syn- and anti-propionate aldols without diastereoselection in the chiral oxazaborolidinone-promoted aldol reaction with a silyl ketene acetal derived from ethyl 2-(methylthio)propionate
Abu Hena, M
Terauchi, S
Kim, CS
Horiike, M
Kiyooka, S
TETRAHEDRON-ASYMMETRY, 1998, 9 (11) : 1883 - 1890
[2] ALDOL CONDENSATIONS OF ETHYL 1,3-DITHIOLANE-2-CARBOXYLATE AND ETHYL 1,3-DITHIANE-2-CARBOXYLATE WITH CHIRAL ALDEHYDES - EXCEPTIONAL DIASTEREOFACE SELECTIVITY FROM 2 CONVENIENT ACETATE EQUIVALENTS
FLIPPIN, LA
DOMBROSKI, MA
TETRAHEDRON LETTERS, 1985, 26 (25) : 2977 - 2980
[3] New Strategy for the Synthesis of Some Valuable Chiral 1,3-Diols with High Enantiomeric Purity: New Organocatalyst, Asymmetric Aldol Reaction, and Reduction
Yildiz, Tulay
Hasdemir, Belma
Yasa, Hasniye
Kucuk, Hatice Baspinar
ACS OMEGA, 2024, 9 (11): : 12657 - 12664

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