Financial support for this work has been provided by the NIH/NIGMS (GM073072). We thank Abbott Laboratories, Amgen, 3M, and Boerhinger–Ingelheim for generous research support and Wacker Chemical Corp., FMCLithium, and BASF for reagent support. K.A.S. is a fellow of the A. P. Sloan Foundation. Funding for the NU Analytical Services Laboratory has been furnished in part by the NSF (CHE-9871268). T.E.R. is a recipient of a 2007–2008 ACS Division of Organic Chemistry fellowship sponsored by Bristol-Myers Squibb.
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Communication
Catalytic Enantioselective α-Acylvinyl Anion Reactions of Silyloxyallenes†
Article first published online: 11 SEP 2007
DOI: 10.1002/anie.200702818
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Reynolds, T. and Scheidt, K. (2007), Catalytic Enantioselective α-Acylvinyl Anion Reactions of Silyloxyallenes. Angewandte Chemie International Edition, 46: 7806–7809. doi: 10.1002/anie.200702818
- †
Publication History
- Issue published online: 4 OCT 2007
- Article first published online: 11 SEP 2007
- Manuscript Revised: 20 JUL 2007
- Manuscript Received: 26 JUN 2007
Funded by
- NIH/NIGMS. Grant Number: GM073072
- NSF. Grant Number: CHE-9871268
Keywords:
- acylvinyl anions;
- asymmetric catalysis;
- chromium;
- silicon;
- synthetic methods
Graphical Abstract
Alternatives with silicon: The enantioselective Lewis acid catalyzed addition of racemic silyloxyallenes to aldehydes is reported. A {(salen)CrIII} complex efficiently catalyzes the reaction of these α-acylvinyl anion equivalents (see scheme) with excellent enantioselectivity, high yield, and superb control over the configuration of the resulting double bond.