Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes

Synthesis and Chemistry of Bridgehead Allylsilanes. Stereoselective Reactions with Aldehydes

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.

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Veröffentlicht in:Organic letters 2005-09, Vol.7 (18), p.3913-3916
Hauptverfasser: Lauchli, Ryan, Whitney, John M, Zhu, Liang, Shea, Kenneth J
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Catalysis
Molecular Structure
Silanes - chemical synthesis
Silanes - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051363c