Financial support was provided by the National Institutes of Health (GM 58133). N.Z.B. was the recipient of a Pfizer Summer Undergraduate Research Fellowship and an NSF-REU Fellowship. I.A.P. was supported by the Irving Langmuir Scholars Program. We are grateful to Amgen, Merck Research Laboratories, and the Arthur C. Cope Fund for unrestricted research support as well.
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Communication
The Enantioselective Allylation and Crotylation of Sterically Hindered and Functionalized Aryl Ketones: Convenient Access to Unusual Tertiary Carbinol Structures†
Article first published online: 3 MAY 2006
DOI: 10.1002/anie.200600910
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Burns, N. Z., Hackman, B. M., Ng, P. Y., Powelson, I. A. and Leighton, J. L. (2006), The Enantioselective Allylation and Crotylation of Sterically Hindered and Functionalized Aryl Ketones: Convenient Access to Unusual Tertiary Carbinol Structures. Angewandte Chemie International Edition, 45: 3811–3813. doi: 10.1002/anie.200600910
- †
Publication History
- Issue published online: 24 MAY 2006
- Article first published online: 3 MAY 2006
- Manuscript Received: 8 MAR 2006
Keywords:
- allylation;
- allylsilanes;
- crotylation;
- enantioselectivity;
- ketones
Graphical Abstract
A strained allylsilane reagent is highly effective in the enantioselective allylation of hydroxyphenylketones. The method is uniquely tolerant both of sterically hindered aliphatic ketones and highly functionalized diaryl ketones and has been extended to include the first examples of highly diastereo- and enantioselective ketone crotylation, which provides access to both diastereomers.