Lewis base activation of Lewis acids: Catalytic, enantioselective addition of glycolate-derived silyl ketene acetals to aldehydes

被引：53

作者：

Denmark, Scott E. ^{[1
]}

Chung, Won-jin ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 12期

关键词：

D O I：

10.1021/jo8006539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic system involving silicon tetrachloride and a chiral, Lewis basic bisphosphoramide catalyst is effective for the addition of glycolate-derived silyl ketene acetals to aldehydes. It was found that the sense of diastereoselectivity could be modulated by changing the size of the substituents on the silyl ketene acetals. In general, the trimethylsilyl ketene acetals derived from methyl glycolates with a large protecting group on the alpha-oxygen provide enantiomerically enriched alpha,beta-dihydroxy esters with high syn-diastereoselectivity, whereas the tent-butyldimethylsilyl ketene acetals derived from bulky esters of a-methoxyacetic acid provide enantiomerically enriched alpha,beta-dihydroxy esters with high anti-diastereoselecitvity.

引用

页码：4582 / 4595

页数：14

共 50 条

[1] ORGN 441-Lewis base activation of Lewis acids: Catalytic, enantioselective addition of glycolate derived silyl ketene acetals to aldehydes
Denmark, Scott E.
Chung, Won-jin
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[2] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
Beutner, GL
Wynn, T
Eastgate, MD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) : 3774 - 3789
[3] Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
[J]. Denmark, S.E. (denmark@scs.uiuc.edu), 1600, American Chemical Society (127):
[4] Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes
Denmark, SE
Wynn, T
Beutner, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13405 - 13407
[5] Lewis base catalyzed addition of silyl ketene acetals to aldehydes.
Denmark, SE
Beutner, GL
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U106 - U106
[6] Lewis base activation of Lewis acids.: Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes
Denmark, SE
Heemstra, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) : 1038 - 1039
[7] Lewis base activation of Lewis acids. Vinylogous aldol addition reactions of conjugated N,O-silyl ketene acetals to aldehydes
Denmark, Scott E.
Heemstra, Jr., John R.
[J]. Journal of the American Chemical Society, 2006, 128 (04): : 1038 - 1039
[8] Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions
Denmark, Scott E.
Chung, Won-Jin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1890 - 1892
[9] Lewis base activation of Lewis acids. Catalytic enantioselective addition of silyl enol ethers of achiral methyl ketones to aldehydes
Denmark, SE
Heemstra, JR
[J]. ORGANIC LETTERS, 2003, 5 (13) : 2303 - 2306
[10] Lewis base activation of Lewis acids: Catalytic enantioselective allylation and propargylation of aldehydes
Denmark, SE
Wynn, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) : 6199 - 6200

← 1 2 3 4 5 →