Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 20, Pages 6932-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja901915u
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Funding
- University of Toronto
- Canada Foundation for Innovation
- Ontario Research Fund
- NSERC
- Boehringer Ingelheim (Canada) Ltd.
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This communication describes the first rhodium-catalyzed intramolecular olefin hydroacylation to produce medium-sized heterocyclic ketones with high regio- and enantiocontrol. Both alpha- and beta-substituted ketones can be produced, depending on catalyst choice and substrate structure. In this stereoselective C-H bond functionalization, ethers, sulfides, and sulfoxides function as effective directing groups. Results from an isotopic labeling study suggest reductive elimination is not the turnover-limiting step in this olefin hydroacylation; thus, the proposed mechanism is distinct from those previously reported.
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