Enantioselective reduction of esters: synthesis of optically active α-acetoxy ethers

An enantioselective reduction and acetylation of esters to α-acetoxy ethers is described. Reduction with a NaAlH 4–ephedrine reagent followed by in situ acetylation gives 2 with good enantiomeric excess. This reaction is limited in scope, but it demonstrates that enantioselective reductions of ester...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 19; pp. 3593 - 3596
Main Authors Rychnovsky, Scott D, Bax, Brian M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.05.2000
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
ASYMMETRIC-SYNTHESIS
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Summary:An enantioselective reduction and acetylation of esters to α-acetoxy ethers is described. Reduction with a NaAlH 4–ephedrine reagent followed by in situ acetylation gives 2 with good enantiomeric excess. This reaction is limited in scope, but it demonstrates that enantioselective reductions of esters are possible.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00470-6