Synlett 1996; 1996(8): 757-758
DOI: 10.1055/s-1996-5514
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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.