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CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids.
Org Lett. 2020 Jul 17; 22(14):5666-5670.OL

Abstract

The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides.

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

Language

eng

PubMed ID

32628019

Citation

Link, Achim, et al. "CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids." Organic Letters, vol. 22, no. 14, 2020, pp. 5666-5670.
Link A, Zhou Y, Buchwald SL. CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids. Org Lett. 2020;22(14):5666-5670.
Link, A., Zhou, Y., & Buchwald, S. L. (2020). CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids. Organic Letters, 22(14), 5666-5670. https://doi.org/10.1021/acs.orglett.0c02064
Link A, Zhou Y, Buchwald SL. CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids. Org Lett. 2020 Jul 17;22(14):5666-5670. PubMed PMID: 32628019.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - CuH-Catalyzed Asymmetric Reductive Amidation of α,β-Unsaturated Carboxylic Acids. AU - Link,Achim, AU - Zhou,Yujing, AU - Buchwald,Stephen L, Y1 - 2020/07/06/ PY - 2020/7/7/pubmed PY - 2020/7/7/medline PY - 2020/7/7/entrez SP - 5666 EP - 5670 JF - Organic letters JO - Org. Lett. VL - 22 IS - 14 N2 - The direct enantioselective copper hydride (CuH)-catalyzed synthesis of β-chiral amides from α,β-unsaturated carboxylic acids and secondary amines under mild reaction conditions is reported. The method utilizes readily accessible carboxylic acids and tolerates a variety of functional groups in the β-position including several heteroarenes. A subsequent iridium-catalyzed reduction to γ-chiral amines can be performed in the same flask without purification of the intermediate amides. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32628019/CuH-Catalyzed_Asymmetric_Reductive_Amidation_of_α,β-Unsaturated_Carboxylic_Acids L2 - https://doi.org/10.1021/acs.orglett.0c02064 DB - PRIME DP - Unbound Medicine ER -
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