Synthesis of Homochiral N-Protected β-Amino Sulfoxides from α-Amino Alcohols

Renata Siedlecka; Jacek Skarzewski

doi:10.1055/s-1996-5514

Synlett 1996; 1996(8): 757-758
DOI: 10.1055/s-1996-5514

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Synthesis of Homochiral N-Protected β-Amino Sulfoxides from α-Amino Alcohols

Renata Siedlecka, Jacek Skarzewski^*

^*Institute of Organic Chemistry, Biochemistry and Biotechnology, Technical University, 50-370 Wroclaw, Poland, Fax +(4871)224064; E-mail skarzewski@kchf.ch.pwr.wroc.pl

Abstract

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A facile method for the preparation of the title compounds is described. Homochiral N-protected β-amino alcohols are smoothly converted into the corresponding sulfides 1. The two-phase oxidation of sulfides (R)-1 with sodium hypochlorite mediated by TEMPO and co-catalyzed by KBr leads exclusively to the corresponding sulfoxides, (R,S _S)-2 (minor) and (R,R _S)-3 (major, up to 88 % d.e.). Both products are easily separated and purified by chromatography or recrystallization.

β-amino sulfides - β-amino sulfoxides - oxidation - diastereoselectivity

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