Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution

被引：27

作者：

Hara, Keiichi ^{[1
]}

Tosaki, Shin-Ya ^{[1
]}

Gnanadesikan, Vijay ^{[1
]}

Morimoto, Hiroyuki ^{[1
]}

Harada, Shinji ^{[1
]}

Sugita, Mari ^{[1
]}

Yamagiwa, Noriyuki ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 26期

关键词：

Asymmetric catalysis; Bifunctional catalysis; Kinetic resolution; Nitroaldol; Tertiary alcohol; ASYMMETRIC HENRY REACTION; MANNICH-TYPE REACTIONS; THIOUREA BIFUNCTIONAL ORGANOCATALYST; ALPHA-HYDROXY ESTERS; COMBINATORIAL APPROACH; KINETIC RESOLUTION; LANTHANIDE COMPLEXES; CINCHONA ALKALOIDS; ALDOL CONDENSATION; ACHIRAL ADDITIVES;

D O I：

10.1016/j.tet.2009.02.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using a 2:1 mixture of La-Li-3-(binaphthoxide 1a)(3) complex (LLB) and La-Li-3-(biphenoxide 1e)(3) complex, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Transformations of products were also investigated. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5030 / 5036

页数：7

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