Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Authors
Hanaki, N Link, JT MacMillan, DWC Overman, LE Trankle, WG Wurster, JA
Citation
N. Hanaki et al., Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral, ORG LETT, 2(2), 2000, pp. 223-226
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
2
Year of publication
2000
Pages
223 - 226
Database
ISI
SICI code
1523-7060(20000127)2:2<223:SITPSO>2.0.ZU;2-C
Abstract
The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins- pinacol condensation of this type is the central strategic step in an enant ioselective synthesis of (-)-citreoviral.