A Highly Diastereo- and Enantioselective Copper(I)-Catalyzed Henry Reaction Using a Bis(sulfonamide)-Diamine Ligand

被引：120

作者：

Jin, Wei ^{[1
]}

Li, Xincheng ^{[1
]}

Wan, Boshun ^{[1
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 02期

关键词：

ASYMMETRIC NITROALDOL REACTION; THIOUREA BIFUNCTIONAL ORGANOCATALYST; SALEN-CHROMIUM COMPLEXES; CU-II; COPPER(II) COMPLEXES; HYDROXYNITRILE LYASE; ATOM ECONOMY; BASE COMPLEX; CATALYST; GUANIDINE;

D O I：

10.1021/jo101932a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral alpha-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantioselectivity (up to 99%). Moreover, with the assistance of pyridine, a CuBr-3a system promotes the diastereoselective Henry reaction with various aldehyde substrates and gives the corresponding syn-selective adduct with up to a 99% yield and 32.3:1 syn/anti selectivity. The enantiomeric excess of the syn adduct was 97%.

引用

页码：484 / 491

页数：8

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