Synthesis and chemistry of bridgehead allylsilanes. Stereoselective reactions with aldehydes

Ryan Lauchli; John M Whitney; Liang Zhu; Kenneth J Shea

doi:10.1021/ol051363c

Synthesis and chemistry of bridgehead allylsilanes. Stereoselective reactions with aldehydes

Org Lett. 2005 Sep 1;7(18):3913-6. doi: 10.1021/ol051363c.

Authors

Ryan Lauchli¹, John M Whitney, Liang Zhu, Kenneth J Shea

Affiliation

¹ Department of Chemistry, 516 Rowland Hall, University of California-Irvine, Irvine, CA 92697-2025, USA.

PMID: 16119930
DOI: 10.1021/ol051363c

Abstract

A type II intramolecular Diels-Alder reaction provides access to bicyclo[5.3.1] ring systems with an imbedded bridgehead allylsilane. The Lewis acid catalyzed reactions of these compounds with aldehydes proceed efficiently and with control of stereochemistry. [reaction: see text]

Publication types

Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Aldehydes / chemistry*
Catalysis
Molecular Structure
Silanes / chemical synthesis*
Silanes / chemistry*
Stereoisomerism

Substances

Aldehydes
Silanes