These authors contributed equally to this work.
Enantiodivergent and γ-Selective Asymmetric Allylic Amination†
Article first published online: 27 JAN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 10, pages 2382–2386, March 5, 2012
How to Cite
Wang, J., Chen, J., Kee, C. W. and Tan, C.-H. (2012), Enantiodivergent and γ-Selective Asymmetric Allylic Amination. Angew. Chem. Int. Ed., 51: 2382–2386. doi: 10.1002/anie.201107317
This work was supported by ARF grant R-143-000-461-112 and scholarships (to J.M. and C.W.K) from the National University of Singapore.
- Issue published online: 1 MAR 2012
- Article first published online: 27 JAN 2012
- Manuscript Revised: 21 DEC 2011
- Manuscript Received: 17 OCT 2011
- National University of Singapore. Grant Number: R-143-000-461-112
- allylic compounds;
- asymmetric synthesis;
- homogeneous catalysis;
- synthetic methods
Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive.