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Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles.
J Am Chem Soc. 2009 May 27; 131(20):6932-3.JA

Abstract

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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Authors+Show Affiliations

Coulter MM
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Dornan PK
No affiliation info available
Dong VM
No affiliation info available

MeSH

AcylationAldehydesAlkenesBenzaldehydesCatalysisCyclizationHeterocyclic CompoundsKetonesRhodiumStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19415904

Citation

Coulter, Matthew M., et al. "Rh-catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-membered Heterocycles." Journal of the American Chemical Society, vol. 131, no. 20, 2009, pp. 6932-3.
Coulter MM, Dornan PK, Dong VM. Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles. J Am Chem Soc. 2009;131(20):6932-3.
Coulter, M. M., Dornan, P. K., & Dong, V. M. (2009). Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles. Journal of the American Chemical Society, 131(20), 6932-3. https://doi.org/10.1021/ja901915u
Coulter MM, Dornan PK, Dong VM. Rh-catalyzed Intramolecular Olefin Hydroacylation: Enantioselective Synthesis of Seven- and Eight-membered Heterocycles. J Am Chem Soc. 2009 May 27;131(20):6932-3. PubMed PMID: 19415904.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh-catalyzed intramolecular olefin hydroacylation: enantioselective synthesis of seven- and eight-membered heterocycles. AU - Coulter,Matthew M, AU - Dornan,Peter K, AU - Dong,Vy M, PY - 2009/5/7/entrez PY - 2009/5/7/pubmed PY - 2009/7/2/medline SP - 6932 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 131 IS - 20 N2 - 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/19415904/Rh_catalyzed_intramolecular_olefin_hydroacylation:_enantioselective_synthesis_of_seven__and_eight_membered_heterocycles_ L2 - https://doi.org/10.1021/ja901915u DB - PRIME DP - Unbound Medicine ER -