Subtilisin-catalyzed resolution of N-acyl arylsulfinamides

…, VP Magloire, RJ Kazlauskas

Index: Savile, Christopher K.; Magloire, Vladimir P.; Kazlauskas, Romas J. Journal of the American Chemical Society, 2005 , vol. 127, # 7 p. 2104 - 2113

Full Text: HTML

Citation Number: 40

Abstract

We report the first biocatalytic route to sulfinamides (RS (O)-NH2), whose sulfur stereocenter makes them important chiral auxiliaries for the asymmetric synthesis of amines. Subtilisin E did not catalyze hydrolysis of N-acetyl or N-butanoyl arylsulfinamides, but did catalyze a highly enantioselective (E> 150 favoring the (R)-enantiomer) hydrolysis of N-chloroacetyl and N-dihydrocinnamoyl arylsulfinamides. Gram-scale resolutions using subtilisin E ...