Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols to Access Propargylic Stereocenters

Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols to Access Propargylic Stereocenters
Christine S. Nervig, Matthew S. Sigman, Zhi-Min Chen, Ryan J. DeLuca
An enantioselective redox-relay Heck alkynylation of di- and trisubstituted alkenols to construct propargylic stereocenters is disclosed using a new pyridine oxazoline ligand. This strategy allows direct access to chiral β-alkynyl carbonyl compounds employing allylic alcohol substrates in contrast to more traditional conjugate addition methods. Heck alkynylation: A convenient redox-relay Heck strategy to synthesize enantiomerically enriched β-alkynyl carbonyl compounds from allylic alcohols with high functional group tolerance is described. Trisubstituted allylic alcohols are also promising substrates allowing for the formation of propargylic quaternary stereocenters.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703089

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