Asymmetric syn-selective Henry reaction catalyzed by the sulfonyldiamine-CuCl-pyridine system

被引：112

作者：

Arai, Takayoshi ^{[1
]}

Takashita, Ryuta ^{[1
]}

Endo, Yoko ^{[1
]}

Watanabe, Masahiko ^{[1
]}

Yanagisawa, Akira ^{[1
]}

机构：

[1] Chiba Univ, Dept Chem, Grad Sch Sci, Inage Ku, Chiba 2638522, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 13期

关键词：

D O I：

10.1021/jo800412x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic asymmetric Henry reaction has been developed with use of a sulfonyldiamine-CuCl complex as a catalyst. A series of new binaphthyl-containing sulfonyldiamine ligands (2a-h) were readily synthesized in two steps starting from commercially available chiral 1,2-diamines. The (R,R)-diamine-(R)-binaphthyl ligand (2d)-CuCl complex smoothly catalyzed the enantioselective Henry reaction with the assistance of pyridine to give the corresponding adduct with high enantiomeric excess (up to 93%). Moreover, the 2d-CuCl-pyridine system promotes the diastereoselective Henry reaction in syn-selective manner to give the adduct in up to 99% yield with 92:8 syn/anti selectivity. The enantiomeric excess of the syn-adduct was 84% ee.

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页码：4903 / 4906

页数：4

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