We thank Dr. S. K. Lam for first suggesting experiments using optically pure epoxy enolsilanes. Support from the Research Grants Council of Hong Kong (GRF HKU 7015/10P) and The University of Hong Kong are gratefully acknowledged.
Asymmetric (4+3) Cycloadditions of Enantiomerically Enriched Epoxy Enolsilanes†
Article first published online: 24 OCT 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 48, pages 12120–12123, November 26, 2012
How to Cite
Lo, B., Lam, S., Wong, W.-T. and Chiu, P. (2012), Asymmetric (4+3) Cycloadditions of Enantiomerically Enriched Epoxy Enolsilanes . Angew. Chem. Int. Ed., 51: 12120–12123. doi: 10.1002/anie.201207427
- Issue published online: 21 NOV 2012
- Article first published online: 24 OCT 2012
- Manuscript Received: 14 SEP 2012
- Research Grants Council of Hong Kong. Grant Number: GRF HKU 7015/10P
- The University of Hong Kong
- allylic compounds;
- synthetic methods
A f(oxy) allyl: The intermolecular (4+3) cycloaddition of enantiomerically enriched epoxy enolsilanes produces cycloadducts with up to 99 % ee, thus implying the reaction does not proceed by the putative achiral oxyallyl cation intermediate, but through a transiently chiral electrophile which retains the stereochemical information of the epoxide (see scheme; TES=triethylsilyl, Tf=trifluoromethanesulfonyl).