Asymmetric Henry Reaction Catalyzed by Novel Chiral Bioxazolines from Tartaric Acid

被引：18

作者：

Balaraman, Kaluvu ^{[1
]}

Vasanthan, Ravichandran ^{[1
]}

Kesavan, Venkitasamy ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Biotechnol, Biol Chem Lab, Bhupat & Jyothi Mehta Sch, Madras 600036, Tamil Nadu, India

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 15期

关键词：

asymmetric catalysis; aldol reactions; heterocyclic compounds; nitro compounds; alcohols; BIS-OXAZOLINE LIGANDS; ALPHA-HYDROXY ESTERS; BIS(OXAZOLINE) LIGANDS; COPPER(II) COMPLEXES; BISOXAZOLINE LIGANDS; NITROALDOL REACTIONS; CHELATE SIZE; CYCLOPROPANATION; ENANTIOSELECTIVITY; HYDROSILYLATION;

D O I：

10.1055/s-0031-1289811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel C-2-symmetric chiral bioxazolines were synthesized in good yields by the fusion of optically active acids with a tartaric acid derivative. Complexes of these products with copper(II) acetate monohydrate were found to be excellent catalysts for the Henry reaction, giving various nitro alcohols in very good yields and up to 84% enantiomeric excess. Although only five-membered chelation is possible with these ligands, they give better enantioselectivities than other bioxazoline ligands that undergo similar coordination.

引用

页码：2455 / 2462

页数：8

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