Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 6, Pages 1634-1638Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611306
Keywords
asymmetric catalysis; heterocycles; indium; organocatalysis; synergistic catalysis
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Funding
- Aarhus University
- Carlsberg Foundation
- FNU
- European Commission for a Marie Curie Intra European Fellowship for Career Development [PIEF-GA-2013-622413]
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A novel alkyl functionalization of unactivated alkyl quinolines has been developed combining InCl3 activation with organocatalytic activation of ,-unsaturated aldehydes in a synergistic fashion. The reaction proceeds in a highly stereoselective manner as a sequence involving two consecutive synergistic catalytic cycles (Lewis acid- and iminium ion-catalyzed) and requires neither pre-activated alkyl quinoline substrates with electron-withdrawing substituents nor highly activated electrophiles. The reaction provides selectively double- or mono-addition products in good yields and high to excellent stereoselectivities. Furthermore, based on spectroscopic and labelling experiments, the mechanisms for the reactions are discussed.
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