Tags

Type your tag names separated by a space and hit enter

Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.
J Am Chem Soc. 2017 06 21; 139(24):8126-8129.JA

Abstract

The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner.

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

Language

eng

PubMed ID

28565905

Citation

Zhou, Yujing, et al. "Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates." Journal of the American Chemical Society, vol. 139, no. 24, 2017, pp. 8126-8129.
Zhou Y, Bandar JS, Buchwald SL. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. J Am Chem Soc. 2017;139(24):8126-8129.
Zhou, Y., Bandar, J. S., & Buchwald, S. L. (2017). Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. Journal of the American Chemical Society, 139(24), 8126-8129. https://doi.org/10.1021/jacs.7b04937
Zhou Y, Bandar JS, Buchwald SL. Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. J Am Chem Soc. 2017 06 21;139(24):8126-8129. PubMed PMID: 28565905.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates. AU - Zhou,Yujing, AU - Bandar,Jeffrey S, AU - Buchwald,Stephen L, Y1 - 2017/06/06/ PY - 2017/6/2/pubmed PY - 2018/5/29/medline PY - 2017/6/2/entrez SP - 8126 EP - 8129 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 139 IS - 24 N2 - The direct asymmetric copper hydride (CuH)-catalyzed coupling of α,β-unsaturated carboxylic acids to aryl alkenes to access chiral α-aryl dialkyl ketones is reported. A variety of substrate substitution patterns, sensitive functional groups, and heterocycles are tolerated in this reaction, which significantly expands the range of accessible products compared with existing hydroacylation methodology. Although mechanistic studies are ongoing, we propose that CuH-catalyzed silylation of unsaturated acids occurs to access a uniquely effective acyl electrophilic coupling partner. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/28565905/Enantioselective_CuH_Catalyzed_Hydroacylation_Employing_Unsaturated_Carboxylic_Acids_as_Aldehyde_Surrogates_ L2 - https://dx.doi.org/10.1021/jacs.7b04937 DB - PRIME DP - Unbound Medicine ER -