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Synlett 1996; 1996(8): 757-758
DOI: 10.1055/s-1996-5514
DOI: 10.1055/s-1996-5514
letter
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Synthesis of Homochiral N-Protected β-Amino Sulfoxides from α-Amino Alcohols
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199608/lookinside/thumbnails/10.1055-s-1996-5514-1.jpg)
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