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|Title: ||Asymmetric synthesis of beta-amino acids through application of chiral sulfoxide|
|Authors: ||SIVAKUMAR, AV|
|Keywords: ||convenient method|
|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 . .|
|Appears in Collections:||Article|
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