Enantioselective aldol condensation of O-silyl dienolates to aldehydes mediated by chiral BINOL-titanium complexes

Citation
M. De Rosa et al., Enantioselective aldol condensation of O-silyl dienolates to aldehydes mediated by chiral BINOL-titanium complexes, TETRAHEDR-A, 11(15), 2000, pp. 3187-3195
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
15
Year of publication
2000
Pages
3187 - 3195
Database
ISI
SICI code
0957-4166(20000811)11:15<3187:EACOOD>2.0.ZU;2-O
Abstract
Chiral BINOL-titanium complexes have been shown to catalyze enantioselectiv e aldol reactions between dioxinone derivatives and a set of aldehydes. The aldol adducts are isolated in good yields and high enantioselectivities. A range of substitution patterns on the O-silyl dienolate is possible: alkyl and benzyl substituents are tolerated. A simple reaction protocol is descr ibed and provides an efficient alternative to the well-known methods for co nducting enantioselective Mukaiyama aldol reactions. (C) 2000 Elsevier Scie nce Ltd. All rights reserved.