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Enantioselective Synthesis of Quaternary alpha-Aminophosphonates via Conjugate Addition of alpha-Nitrophosphonates to Enones

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Title Enantioselective Synthesis of Quaternary alpha-Aminophosphonates via Conjugate Addition of alpha-Nitrophosphonates to Enones
 
Creator BERA, K
NAMBOOTHIRI, INN
 
Subject PHOSPHONIC ACID-DERIVATIVES
CATALYTIC ASYMMETRIC ALLYLATION
AMINO PHOSPHONATES
MICHAEL ADDITION
STEREOSELECTIVE-SYNTHESIS
BETA-AMINOPHOSPHONATES
HYDROPHOSPHONYLATION
IMINES
ORGANOCATALYSTS
IMINOPHOSPHONATES
 
Description Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-17T04:54:46Z
2014-10-17T04:54:46Z
2012
 
Type Article
 
Identifier ORGANIC LETTERS, 14(4)980-983
http://dx.doi.org/10.1021/ol203132h
http://dspace.library.iitb.ac.in/jspui/handle/100/16001
 
Language en