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Full Paper
Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Indolylnitroalkenes
Article first published online: 4 JAN 2012
DOI: 10.1002/ejoc.201101648
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Xing, J., Chen, G., Cao, P. and Liao, J. (2012), Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Indolylnitroalkenes. Eur. J. Org. Chem., 2012: 1230–1236. doi: 10.1002/ejoc.201101648
Publication History
- Issue published online: 13 FEB 2012
- Article first published online: 4 JAN 2012
- Manuscript Received: 15 NOV 2011
Funded by
- National Natural Science Foundation of China. Grant Numbers: 21072186, 20872139
- West Light Foundation of CAS
- National Basic Research Program of China. Grant Number: 2010CB833300
- Chengdu Institute of Biology, CAS. Grant Number: Y0B1051100
Keywords:
- Synthetic methods;
- Asymmetric synthesis;
- Homogeneous catalysis;
- Rhodium;
- Heterocycles
Abstract
Indolylnitroethanes and their derivatives are key intermediates to many bioactive structures. Most approaches to access chiral indolylnitroethanes involve organocatalyzed or metal-catalyzed asymmetric Friedel–Crafts reaction of indoles with nitroalkenes. We have developed an efficient approach to optically pure α-aryl-3-indolylnitroethanes through rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to indolylnitroalkenes. Excellent yields (up to 99 %) and enantiomeric excesses (up to 99 % ee) of chiral indolylnitroethanes were achieved under mild conditions.