Support has been provided in part by the NSF (CHE-0348979), the PRF (Type G), and Northwestern University. We thank Abbott Laboratories, Amgen, AstraZeneca, GlaxoSmithKline, 3M, and Boehringer-Ingelheim for generous unrestricted research support, Wacker Chemical Corp. and FMCLithium for providing reagents, and Troy Reynolds (NU) for assistance with X-ray crystallography. K.A.S. is a fellow of the Alfred P. Sloan Foundation.
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Communication
Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes†
Article first published online: 12 FEB 2008
DOI: 10.1002/anie.200705229
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lettan, R., Woodward, C. and Scheidt, K. (2008), Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes. Angewandte Chemie International Edition, 47: 2294–2297. doi: 10.1002/anie.200705229
- †
Publication History
- Issue published online: 3 MAR 2008
- Article first published online: 12 FEB 2008
- Manuscript Received: 14 NOV 2007
Funded by
- NSF. Grant Number: CHE-0348979
- PRF
- Northwestern University
Keywords:
- γ-lactams;
- acylsilanes;
- chiral auxiliaries;
- homoenolates;
- synthetic methods
Graphical Abstract
It takes three: The stereoselective synthesis of highly substituted γ-lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ-amino-β-hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ-lactams in excellent yields.