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Enantioselective Synthesis of alpha-Amino-gamma-sulfonyl Phosphonates with a Tetrasubstituted Chiral alpha-Carbon via Quinine-Squaramide-Catalyzed Michael Addition of Nitrophosphonates to Vinyl Sulfones

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Title Enantioselective Synthesis of alpha-Amino-gamma-sulfonyl Phosphonates with a Tetrasubstituted Chiral alpha-Carbon via Quinine-Squaramide-Catalyzed Michael Addition of Nitrophosphonates to Vinyl Sulfones
 
Creator BERA, K
NAMBOOTHIRI, INN
 
Subject amino phosphonates
amino sulfones
asymmetric catalysis
Michael addition
squaramides
ASYMMETRIC CONJUGATE ADDITIONS
AMINOPHOSPHONIC ACIDS
ORGANOPHOSPHORUS COMPOUNDS
STEREOSELECTIVE-SYNTHESIS
BETA-AMINOPHOSPHONATES
ORGANIC-SYNTHESIS
ORGANOCATALYSTS
DERIVATIVES
NITROOLEFINS
ALDEHYDES
 
Description -Nitro--sulfonyl phosphonates with a key tetrasubstituted chiral -carbon center have been synthesized for the first time in high yield and enantioselectivity through a quinine-squaramide-catalyzed conjugate addition of -nitro phosphonates to aryl vinyl sulfones. Representative examples presented here for the transformation of nitrosulfonyl phosphonates to aminosulfonyl phosphonates, alkylation at the -position of the sulfonyl group followed by desulfonation and scale-up of the conjugate addition highlight the practical applications of the methodology.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-10-17T04:54:15Z
2014-10-17T04:54:15Z
2013
 
Type Article
 
Identifier ADVANCED SYNTHESIS & CATALYSIS, 355(7)1265-1270
http://dx.doi.org/10.1002/adsc.201300224
http://dspace.library.iitb.ac.in/jspui/handle/100/16000
 
Language en