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Communication
Asymmetric Conjugate Addition of Azide to α,β-Unsaturated Carbonyl Compounds Catalyzed by Simple Peptides
Article first published online: 13 OCT 2000
DOI: 10.1002/1521-3773(20001016)39:20<3635::AID-ANIE3635>3.0.CO;2-Y
© 2000 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
39:20<>1.0.CO;2-V/asset/cover.gif?v=1&s=a0b20299cb8b6ed09a4e6b64e13e5ba2c41f6ffe "Angewandte Chemie International Edition")
Additional Information
How to Cite
Horstmann, T., Guerin, D. and Miller, S. (2000), Asymmetric Conjugate Addition of Azide to α,β-Unsaturated Carbonyl Compounds Catalyzed by Simple Peptides . Angewandte Chemie International Edition, 39: 3635–3638. doi: 10.1002/1521-3773(20001016)39:20<3635::AID-ANIE3635>3.0.CO;2-Y
Publication History
- Issue published online: 13 OCT 2000
- Article first published online: 13 OCT 2000
- Manuscript Received: 5 JUN 2000
Keywords:
- additions;
- amino acids;
- asymmetric catalysis;
- metal-free catalysis;
- peptides
Simple tripeptides (A) are asymmetric catalysts for the enantioselective conjugate addition of azide ion to enoate derivatives such as 1. Thus, chiral, nonracemic azides 2 (up to 85 % ee; 97 % yield) may be obtained under mild reaction conditions (toluene, 25°C; TMSN3=trimethylsilyl azide).
