A route to enantiomerically-enriched alpha-silyl aldehydes from 2,3-epoxy alcohols

Authors
Chauret, DC Chong, JM Ye, Q
Citation
Dc. Chauret et al., A route to enantiomerically-enriched alpha-silyl aldehydes from 2,3-epoxy alcohols, TETRAHEDR-A, 10(18), 1999, pp. 3601-3614
Citations number
40
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
18
Year of publication
1999
Pages
3601 - 3614
Database
ISI
SICI code
0957-4166(19990910)10:18<3601:ARTEAA>2.0.ZU;2-5
Abstract
Asymmetric epoxidation of (E)-3-trialkylsilyl-2-propen-1-ols gives the expe cted epoxides with high enantioselectivity. Ring opening reactions of these epoxides with organocopper reagents furnishes 1,2-diols which are readily cleaved with Pb(OAc)(4) to afford alpha-silyl aldehydes with no detectable loss of stereochemistry. (C) 1999 Elsevier Science Ltd. All rights reserved .