We are grateful to the Department of Energy (DE-FG02-05ER15687) for financial support. We thank Dr. E. B. Lobkovsky for X-ray crystallographic assistance, J. M. Rowley for help with in situ IR experiments, and NSERC Canada for financial support to T.L.C.
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Communication
Catalytic Synthesis of β3-Amino Acid Derivatives from α-Amino Acids†
Article first published online: 11 APR 2008
DOI: 10.1002/anie.200705310
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Byrne, C., Church, T., Kramer, J. and Coates, G. (2008), Catalytic Synthesis of β3-Amino Acid Derivatives from α-Amino Acids. Angewandte Chemie International Edition, 47: 3979–3983. doi: 10.1002/anie.200705310
- †
Publication History
- Issue published online: 6 MAY 2008
- Article first published online: 11 APR 2008
- Manuscript Revised: 25 JAN 2008
- Manuscript Received: 19 NOV 2007
Funded by
- Department of Energy. Grant Number: DE-FG02-05ER15687
- NSERC Canada
Keywords:
- amino acids;
- carbonylation;
- cobalt;
- insertion reactions;
- ring expansion
Graphical Abstract
α goes to β! The catalytic ring-expansive carbonylation of oxazolines, easily derived from α-amino acids, to yield β-amino acid derivatives is described. The catalyst is [HCo(CO)4]; high yields are observed for most substrates, and enantiopure oxazolines are carbonylated with predictable stereochemistry to the corresponding enantiopure oxazinones.