Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 35, Pages 10193-10197Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201504749
Keywords
allylation; asymmetric catalysis; diastereodivergence; dual catalysis; regiodivergence
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Funding
- Aarhus University
- Carlsberg Foundation
- European Commission within European Community [PIEF-GA-2013-622413]
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The first asymmetric regio- and diastereodivergent gamma-allylation of cyclic alpha, beta-unsaturated aldehydes based on combined organocatalysis and transition-metal catalysis is disclosed. By combining an aminocatalyst with an iridium catalyst, both diastereomers of branched allylated products can be achieved in moderate to good yields and excellent regio-and stereoselectivities. Furthermore, by replacing the iridium catalyst with a palladium catalyst, the linear allylated products are formed in good yields and excellent regio- and enantioselectivities. The developed method thus provides selective access to all six isomers of the gamma-allylated product in a divergent fashion by choosing the appropriate combination of organo-catalyst, transition-metal catalyst, and ligand.
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