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Enantioselective synthesis of alpha-nitro-delta-ketosulfones via a quinine-squaramide catalyzed conjugate addition of alpha-nitrosulfones to enones

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Title Enantioselective synthesis of alpha-nitro-delta-ketosulfones via a quinine-squaramide catalyzed conjugate addition of alpha-nitrosulfones to enones
 
Creator BERA, K
NAMBOOTHIRI, INN
 
Subject MICHAEL ADDITION
ALPHA,BETA-UNSATURATED ALDEHYDES
VINYL SULFONES
1,3-DIPOLAR CYCLOADDITION
ORGANOCATALYTIC ADDITION
CHIRAL SULFONES
NITROPHOSPHONATES
HYDROGENATION
DERIVATIVES
INHIBITORS
 
Description Conjugate addition of alpha-nitrosulfones to vinyl ketones in the presence of 0.2 mol% of a quinine-squaramide organocatalyst afforded alpha-nitro-delta-ketosulfones possessing a tetrasubstituted chiral center in excellent yield and enantioselectivity in most cases. This strategy also offers a facile and convenient entry into gamma-sulfonylhydroxamates that are one carbon homologs of potent enzyme inhibitors.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-17T04:53:44Z
2014-10-17T04:53:44Z
2013
 
Type Article
 
Identifier CHEMICAL COMMUNICATIONS, 49(90)10632-10634
1359-7345
1364-548X
http://dx.doi.org/10.1039/c3cc45985c
http://dspace.library.iitb.ac.in/jspui/handle/100/15999
 
Language en