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Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids.
J Am Chem Soc. 2016 05 11; 138(18):5821-4.JA

Abstract

A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance.

Authors+Show Affiliations

Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

27121395

Citation

Bandar, Jeffrey S., et al. "Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids." Journal of the American Chemical Society, vol. 138, no. 18, 2016, pp. 5821-4.
Bandar JS, Ascic E, Buchwald SL. Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids. J Am Chem Soc. 2016;138(18):5821-4.
Bandar, J. S., Ascic, E., & Buchwald, S. L. (2016). Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids. Journal of the American Chemical Society, 138(18), 5821-4. https://doi.org/10.1021/jacs.6b03086
Bandar JS, Ascic E, Buchwald SL. Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids. J Am Chem Soc. 2016 05 11;138(18):5821-4. PubMed PMID: 27121395.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective CuH-Catalyzed Reductive Coupling of Aryl Alkenes and Activated Carboxylic Acids. AU - Bandar,Jeffrey S, AU - Ascic,Erhad, AU - Buchwald,Stephen L, Y1 - 2016/04/29/ PY - 2016/4/29/entrez PY - 2016/4/29/pubmed PY - 2018/5/18/medline SP - 5821 EP - 4 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 138 IS - 18 N2 - A new method for the enantioselective reductive coupling of aryl alkenes with activated carboxylic acid derivatives via copper hydride catalysis is described. Dual catalytic cycles are proposed, with a relatively fast enantioselective hydroacylation cycle followed by a slower diastereoselective ketone reduction cycle. Symmetrical aryl carboxyclic anhydrides provide access to enantioenriched α-substituted ketones or alcohols with excellent stereoselectivity and functional group tolerance. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/27121395/Enantioselective_CuH_Catalyzed_Reductive_Coupling_of_Aryl_Alkenes_and_Activated_Carboxylic_Acids_ L2 - https://dx.doi.org/10.1021/jacs.6b03086 DB - PRIME DP - Unbound Medicine ER -