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.

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Duke Authors

Baldwin, Steven W.

Cited Authors

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

Published Date

May 2000

Published In

Organic Letters

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

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