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

Authors
Rychnovsky, SD Bax, BM
Citation
Sd. Rychnovsky et Bm. Bax, Enantioselective reduction of esters: synthesis of optically active alpha-acetoxy ethers, TETRAHEDR L, 41(19), 2000, pp. 3593-3596
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3593 - 3596
Database
ISI
SICI code
0040-4039(20000506)41:19<3593:EROESO>2.0.ZU;2-I
Abstract
An enantioselective reduction and acetylation of esters to alpha-acetoxy et hers is described. Reduction with a NaAlH4-ephedrine reagent followed by in situ acetylation gives 2 with good enantiomeric excess. This reaction is l imited in scope, but it demonstrates that enantioselective reductions of es ters are possible. (C) 2000 Elsevier Science Ltd. All rights reserved.