Diastereoselective reduction of ( S)-1-chloro-3-silyloxybutan-2-one. Synthesis of enantiopure (2 S,3 R) and (2 S,3 S) O-tert-butyldimethylsilyl-3,4-epoxybutan-2-ol

(2 S,3 S)- And (2 R,3 S)-3-[( tert-butyldimethyl)silyloxy]-1-chlorobutan-2-ol have been obtained with high diastereoselectivity by reduction of enantiopure ( S)-3-[( tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corres...

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Bibliographic Details
Published inTetrahedron letters Vol. 40; no. 14; pp. 2863 - 2864
Main Authors Concellón, JoséM., Bernad, Pablo L., Alvarez, R., Rodríguez, A., Baragaña, B.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.04.1999
Elsevier
Subjects
Chemistry
Chemistry, Organic
chiral chloromethyl ketones
diastereoselection
Physical Sciences
reduction
Science & Technology
β,γ-epoxy alcohols
chiral chloromethyl ketones
reduction
diastereoselection
β,γ-epoxy alcohols
beta,gamma-epoxy alcohols
DERIVATIVES
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Summary:(2 S,3 S)- And (2 R,3 S)-3-[( tert-butyldimethyl)silyloxy]-1-chlorobutan-2-ol have been obtained with high diastereoselectivity by reduction of enantiopure ( S)-3-[( tert-butyldimethyl)silyloxy]-1-chlorobutan-2-one using different reducing agents. The chiral alcohols were transformed into the corresponding (2 R,3 S)- and (2 S,3 S)-3-[( tert-butyldimethyl)silyloxy]-1,2-epoxybutane. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(99)00313-5