Benzhydryldimethylsilyl Allylic Silanes:  Syntheses and Applications to [3 + 2] Annulation Reactions

A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with h...

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Bibliographic Details
Published in:Organic letters 2000-05, Vol.2 (10), p.1379-1381
Main Authors: Peng, Zhi-Hui, Woerpel, K. A
Format: Article
Language:English
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Summary:A new silyl group, the benzhydryldimethylsilyl group, has been developed that is easily synthesized and that undergoes facile oxidation. The [3 + 2] annulation reactions of allylic silanes with this silyl group provide a variety of highly substituted five-membered carbocycles and heterocycles with high stereoselectivities. The silyl groups of these cyclic compounds have been oxidized to hydroxyl groups to demonstrate the general synthetic utility of the method.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol005676d