DSpace
 

DSpace at IIT Bombay >
IITB Publications >
Article >

Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/10559

Title: Asymmetric synthesis of beta-amino acids through application of chiral sulfoxide
Authors: SIVAKUMAR, AV
BABU, GS
BHAT, SV
Keywords: convenient method
lactam formation
(+)-thienamycin
chemistry
taxol
Issue Date: 2001
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Citation: TETRAHEDRON-ASYMMETRY, 12(7), 1095-1099
Abstract: 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 . .
URI: 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
ISSN: 0957-4166
Appears in Collections:Article

Files in This Item:

There are no files associated with this item.

View Statistics

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 

Valid XHTML 1.0! DSpace Software Copyright © 2002-2010  Duraspace - Feedback