A solution to the cyclic aldol problem

Journal Article (Journal Article)

[formula: see text] A protocol for achieving stereoselective aldol reactions with cyclic ketones is presented. In terms of yield, the process is particularly effective when a quaternary center at the alpha-carbon of the beta-hydroxy ketone product 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.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; Chen, P; Nikolic, N; Weinseimer, DC

Published Date

  • May 2000

Published In

Volume / Issue

  • 2 / 9

Start / End Page

  • 1193 - 1196

PubMed ID

  • 10810705

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol005525a


  • eng