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. [reaction: see text]
Lauchli
Ryan
R
Department of Chemistry, 516 Rowland Hall, University of California-Irvine, Irvine, CA 92697-2025, USA.
Whitney
John M
JM
Zhu
Liang
L
Shea
Kenneth J
KJ
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D012821:Silanes