A Systematic Study of Chiral Homoprolinols and Their Derivatives in the Catalysis of Enantioselective Addition of Diethylzinc to Aldehydes

被引：9

作者：

Liu, Chang-Lu ^{[1
,2
]}

Wei, Chang-Yong ^{[1
]}

Wang, Shi-Wen ^{[1
]}

Peng, Yun-Gui ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

[2] Sichuan Univ Arts & Sci, Dept Chem & Chem Engn, Dazhou 635000, Peoples R China

来源：

CHIRALITY | 2011年 / 23卷 / 10期

关键词：

gamma-amino alcohol; homoprolinol; enantioselective addition; diethylzinc; ASYMMETRIC ORGANOZINC ADDITIONS; AMINO-ALCOHOLS; GAMMA-AMINO; BETA-AMINO; LIGANDS; BENZALDEHYDE; DIALKYLZINCS; AMINOALCOHOLS; ALKYLATION; REAGENTS;

D O I：

10.1002/chir.21017

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Homoprolinol analogs, a class of optically active gamma-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these gamma-amino alcohols with those by the beta-amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the gamma-amino alcohols are superior to the corresponding beta-amino alcohols when the nitrogen and the oxygen are unsubstituted. Among the homoprolinols we tested, 2b gave the best results (45-88% yields, 44-81% ee) in the addition reactions. To the best of our knowledge, 2b has been noticed as one of the most efficient gamma-amino alcohol catalysts based on pyrrolidine framework. Chirality 23:921-928, 2011. (C) 2011 Wiley-Liss, Inc.

引用

页码：921 / 928

页数：8

共 84 条

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