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CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes.
J Am Chem Soc. 2018 01 17; 140(2):606-609.JA

Abstract

The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations.

Links

Publisher Full Text
ncbi.nlm.nih.gov
dx.doi.org
PMC Free PDF

Authors+Show Affiliations

Zhou Y
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Bandar JS
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Liu RY
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Buchwald SL
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

MeSH

AldehydesCarboxylic AcidsCatalysisCopperMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

29283578

Citation

Zhou, Yujing, et al. "CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes." Journal of the American Chemical Society, vol. 140, no. 2, 2018, pp. 606-609.
Zhou Y, Bandar JS, Liu RY, et al. CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes. J Am Chem Soc. 2018;140(2):606-609.
Zhou, Y., Bandar, J. S., Liu, R. Y., & Buchwald, S. L. (2018). CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes. Journal of the American Chemical Society, 140(2), 606-609. https://doi.org/10.1021/jacs.7b12260
Zhou Y, et al. CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes. J Am Chem Soc. 2018 01 17;140(2):606-609. PubMed PMID: 29283578.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - CuH-Catalyzed Asymmetric Reduction of α,β-Unsaturated Carboxylic Acids to β-Chiral Aldehydes. AU - Zhou,Yujing, AU - Bandar,Jeffrey S, AU - Liu,Richard Y, AU - Buchwald,Stephen L, Y1 - 2018/01/04/ PY - 2017/12/29/pubmed PY - 2018/11/28/medline PY - 2017/12/29/entrez SP - 606 EP - 609 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 140 IS - 2 N2 - The copper hydride (CuH)-catalyzed enantioselective reduction of α,β-unsaturated carboxylic acids to saturated aldehydes is reported. This protocol provides a new method to access a variety of β-chiral aldehydes in good yields, with high levels of enantioselectivity and broad functional group tolerance. A reaction pathway involving a ketene intermediate is proposed based on preliminary mechanistic studies and density functional theory calculations. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/29283578/CuH_Catalyzed_Asymmetric_Reduction_of_αβ_Unsaturated_Carboxylic_Acids_to_β_Chiral_Aldehydes_ L2 - https://dx.doi.org/10.1021/jacs.7b12260 DB - PRIME DP - Unbound Medicine ER -