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

被引：0

作者：

Abu Hena, M

Terauchi, S

Kim, CS

Horiike, M

Kiyooka, S

机构：

[1] Kochi Univ, Dept Chem, Kochi 7808072, Japan

[2] Kochi Univ, Dept Bioresource Sci, Nankoku, Kochi 7830093, Japan

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 11期

关键词：

D O I：

暂无

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A mixture of syn- and anti-aldol products containing an alpha-methylthio group were obtained in good yields with high enantioselectivities in the chiral oxazaborolidinone-promoted aldol reactions of a novel silyl ketene acetal, derived from ethyl 2-(methylthio)propionate, with aldehydes. Subsequent desulfurization resulted in an effective preparation of essentially enantiopure syn- and anti-propionate aldols which were separable. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1883 / 1890

页数：8

共 5 条

[1] 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
Kiyooka, S
Hena, MA
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) : 2181 - 2184
[2] A practical synthesis of essentially enantiopure syn-propionate aldols using a chiral oxazaborolidinone-promoted asymmetric aldol reaction coupled with radical reduction
Kiyooka, S
Shahid, KA
Hena, MA
TETRAHEDRON LETTERS, 1999, 40 (35) : 6447 - 6449
[3] A divergent synthesis of essentially enantiopure syn- and anti-propionate aldol adducts based on the chiral 1,3,2-oxazaborolidin-5-one-promoted asymmetric aldol reaction followed by diastereoselective radical reduction
Kiyooka, S
Shahid, KA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (08) : 1485 - 1495
[4] An efficient method for the synthesis of enantiopure 2,3-anti-propionate aldols involving a 3,5-syn- or anti-diol subunit through chiral borane-mediated enantioselective aldol reaction coupled with radical reduction
Kiyooka, S
Shahid, KA
TETRAHEDRON LETTERS, 2000, 41 (15) : 2633 - 2637
[5] Enantioselective acyclic stereoselection under catalyst control .2. asymmetric synthesis of syn- and anti-1,3-diols incorporating an acetate equivalent by the chiral oxazaborolidinone-catalyzed aldol reaction
Kiyooka, S
Yamaguchi, T
Maeda, H
Kira, H
Hena, MA
Horiike, M
TETRAHEDRON LETTERS, 1997, 38 (20) : 3553 - 3556

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