Enantioselective addition of diethylzinc to aldehydes catalyzed by (R)-1-phenylethylamine-derived 1,4-amino alcohols

被引：16

作者：

Asami, Masatoshi ^{[1
]}

Miyairi, Naomichi ^{[1
]}

Sasahara, Yukihiro ^{[1
]}

Ichikawa, Ken-ichi ^{[1
]}

Hosoda, Naoya ^{[1
]}

Ito, Suguru ^{[1
]}

机构：

[1] Yokohama Natl Univ, Grad Sch Engn, Dept Adv Mat Chem, Hodogaya Ku, Tokiwadai 79-5, Yokohama, Kanagawa 2408501, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 38期

基金：

日本学术振兴会;

关键词：

1,4-Amino alcohols; o-Xylylene structure; 1-Phenylethylamine; Diethylzinc; Chiral secondary alcohols; HIGHLY EFFICIENT CATALYSTS; ASYMMETRIC-SYNTHESIS; CHIRAL LIGANDS; AMINO-ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; AZIRIDINYL ALCOHOLS; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; DIALKYLZINCS; AUXILIARIES;

D O I：

10.1016/j.tet.2015.07.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of o-xylylene-type 1,4-amino alcohols, synthesized from (R)-1-phenylethylamine, were used as chiral ligands for the enantioselective addition of diethylzinc to benzaldehyde. (S)-1-Phenyl-1-propanol was obtained with high enantioselectivity in all cases since the stereochemical outcome of the reaction was controlled by the chiral benzylic carbon bearing amino group. Highest catalytic activity was obtained by using (R)-1-{2-[1-(pyrrolidin-1-yl]ethyl]phenyl}cyclohexan-1-ol (1n) derived from (R)-1-(1-phenylethyl)pyrrolidine and cyclohexanone. Various chiral secondary alcohols were obtained by the reaction of diethylzinc and aldehydes in the presence of in within 2 h with good to high enantioselectivities. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：6796 / 6802

页数：7

共 40 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].