A solution to the cyclic aldol problem

Authors
Baldwin, SW Chen, P Nikolic, N Weinseimer, DC
Citation
Sw. Baldwin et al., A solution to the cyclic aldol problem, ORG LETT, 2(9), 2000, pp. 1193-1196
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
9
Year of publication
2000
Pages
1193 - 1196
Database
ISI
SICI code
1523-7060(20000504)2:9<1193:ASTTCA>2.0.ZU;2-H
Abstract
A protocol for achieving stereoselective aldol reactions with cyclic ketone s is presented. In terms of yield, the process is particularly effective wh en a quaternary center at the alpha-carbon of the beta-hydroxy ketone produ ct is created. The stereochemical outcome, anti or syn, is achieved by the Lewis acid-mediated ring expansion of stereochemically homogeneous epoxides in a reaction related to the pinacol rearrangement.