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. 2007 Mar 1;9(5):943-5.
doi: 10.1021/ol070209i. Epub 2007 Feb 7.

Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane

Tanmay Mandal  1 , Sampak Samanta, Cong-Gui Zhao
Affiliations

Organocatalytic highly enantioselective nitroaldol reaction of alpha-ketophosphonates and nitromethane

Tanmay Mandal et al. Org Lett. .

Abstract

[reaction: see text] 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 (>or=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.

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