Organocatalytic highly enantioselective nitroaldol reaction of α-ketophosphonates and nitromethane

被引：120

作者：

Mandal, Tanmay ^{[1
]}

Samanta, Sampak ^{[1
]}

Zhao, Cong-Gui ^{[1
]}

机构：

[1] Univ Texas, Dept Chem, San Antonio, TX 78249 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 05期

关键词：

D O I：

10.1021/ol070209i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane has been realized by using cupreine (2) or 9-O-benzylcupreine (3) as the catalyst. Both catalysts are highly reactive and highly enantioselective. alpha-Hydroxy-beta-nitrophosphonates have been synthesized in good yields and excellent enantioselectivities (>= 90% ee) at a low catalyst loading (5 mol %). These nitroaldol products may be reduced to the biologically significant beta-amino-alpha-hydroxyphosphonates with complete retention of the stereochemistry.

引用

页码：943 / 945

页数：3

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