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Asymmetric synthesis of beta-amino acids through application of chiral sulfoxide

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Title Asymmetric synthesis of beta-amino acids through application of chiral sulfoxide
 
Creator SIVAKUMAR, AV
BABU, GS
BHAT, SV
 
Subject convenient method
lactam formation
(+)-thienamycin
chemistry
taxol
 
Description This paper describes asymmetric synthesis of beta -aminophenylpropionic acid through application of a homochiral sulfoxide auxiliary. High kinetically controlled (3R.2S.R-S)-diastereoselectivity (-60 degreesC) is achieved during addition of the lithium enolate of tert-butyl (+)-(R)-p-toluenesulfinylacetate to substituted N-(benzylidene)toluene-4-sulfonamides. The reductive cleavage of adduct 3a with sodium amalgam yielded tert-butyl 3-(toluene-4-sulfonamido)-3-phenylpropionate 5a. which was subjected to ester hydrolysis and subsequent detosylation with sodium in liquid ammonia to yield (S)-beta -aminophenylpropionic acid in good yield and high 91% e.e. (C) 2001 . .
 
Publisher PERGAMON-ELSEVIER SCIENCE LTD
 
Date 2011-08-23T15:31:49Z
2011-12-26T12:56:29Z
2011-12-27T05:45:19Z
2011-08-23T15:31:49Z
2011-12-26T12:56:29Z
2011-12-27T05:45:19Z
2001
 
Type Article
 
Identifier TETRAHEDRON-ASYMMETRY, 12(7), 1095-1099
0957-4166
http://dx.doi.org/10.1016/S0957-4166(01)00185-9
http://dspace.library.iitb.ac.in/xmlui/handle/10054/10559
http://hdl.handle.net/10054/10559
 
Language en