This work was supported by a grant from the NSF (CHE-04-53853) and a Focused Funding Award from Johnson & Johnson. We thank Merck Research Laboratories and Amgen for unrestricted support. J.D.H. was the recipient of an NDSEG Fellowship from the Department of Defense, and N.R.P. was supported by a fellowship provided by Boehringer-Ingelheim.
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Communication
Allylsilane–Vinylarene Cross-Metathesis Enables a Powerful Approach to Enantioselective Imine Allylation†
Article first published online: 12 MAR 2008
DOI: 10.1002/anie.200705621
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Huber, J., Perl, N. and Leighton, J. (2008), Allylsilane–Vinylarene Cross-Metathesis Enables a Powerful Approach to Enantioselective Imine Allylation. Angewandte Chemie International Edition, 47: 3037–3039. doi: 10.1002/anie.200705621
- †
Publication History
- Issue published online: 1 APR 2008
- Article first published online: 12 MAR 2008
- Manuscript Received: 8 DEC 2007
Funded by
- NSF. Grant Number: CHE-04-53853
- Focused Funding Award from Johnson & Johnson
- Merck Research Laboratories
- Amgen
- NDSEG Fellowship
- Boehringer-Ingelheim
Keywords:
- allylsilanes;
- asymmetric synthesis;
- cinnamylation;
- cross-coupling;
- homoallylic amines
Graphical Abstract
“Cinnamylation-flavored” synthesis: Cross-metathesis (CM) reactions between an allylsilane and vinylarenes enable the rapid generation of various cinnamylsilanes, which may be used in situ for the highly enantioselective, and diastereodivergent, cinnamylation of imines (see example in scheme). Under this new, simple, and efficient protocol, the potential of imine cinnamylation to produce stereochemically and functionally complex products has been more fully realized. Ar=thienyl, Ar′=2-hydroxyphenyl.