Bifunctional pyridyl alcohols with the bicyclo[3.3.0]octane scaffold in the asymmetric addition of diethylzinc to aldehydes

被引：8

作者：

Zhong, YW ^{[1
]}

Jiang, CS ^{[1
]}

Xu, MH ^{[1
]}

Lin, GQ ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 40期

基金：

中国国家自然科学基金;

关键词：

bicyclo[3.3.0]octane; bifunctional ligand; pyridyl alcohol; diethylzinc; secondary basic site;

D O I：

10.1016/j.tet.2004.07.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some new pyridyl alcohols with the cis-bicyclo[3.3.0] octane scaffold were synthesized and used as chiral ligands for the enantioselective addition of diethylzinc to aldehydes. Ligands 4 were found to be far superior to the C-2-symmetric ligands 2 in terms of enantioselectivities. Quantitative yields and enantiomeric excesses of up to 92% were obtained when the ligand 4 was used. The carbonyl function in 4 proved to be beneficial for the high enantioselectivities in the addition of diethylzinc to aldehydes. Conversion of the carbonyl group into oxime or oxime ether group led to a sort of more active ligands, which catalyzed the same reaction with rate acceleration. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8861 / 8868

页数：8

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