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Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.
J Am Chem Soc. 2003 Mar 26; 125(12):3442-3.JA

Abstract

A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective alpha-hydroxy ketone synthesis.

Authors+Show Affiliations

Miller KM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Huang WS
No affiliation info available
Jamison TF
No affiliation info available

MeSH

AlcoholsAldehydesAlkynesAllyl CompoundsCatalysisKetonesOxidation-ReductionStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

12643701

Citation

Miller, Karen M., et al. "Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and Alpha-hydroxy Ketones." Journal of the American Chemical Society, vol. 125, no. 12, 2003, pp. 3442-3.
Miller KM, Huang WS, Jamison TF. Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones. J Am Chem Soc. 2003;125(12):3442-3.
Miller, K. M., Huang, W. S., & Jamison, T. F. (2003). Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones. Journal of the American Chemical Society, 125(12), 3442-3.
Miller KM, Huang WS, Jamison TF. Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and Alpha-hydroxy Ketones. J Am Chem Soc. 2003 Mar 26;125(12):3442-3. PubMed PMID: 12643701.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones. AU - Miller,Karen M, AU - Huang,Wei-Sheng, AU - Jamison,Timothy F, PY - 2003/3/20/pubmed PY - 2003/5/7/medline PY - 2003/3/20/entrez SP - 3442 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 12 N2 - A highly enantioselective method for catalytic reductive coupling of alkynes and aldehydes is described. Allylic alcohols are afforded with complete E/Z selectivity, generally >95:5 regioselectivity, and in up to 96% ee. In conjunction with ozonolysis, this process is complementary to existing methods of enantioselective alpha-hydroxy ketone synthesis. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12643701/Catalytic_asymmetric_reductive_coupling_of_alkynes_and_aldehydes:_enantioselective_synthesis_of_allylic_alcohols_and_alpha_hydroxy_ketones_ DB - PRIME DP - Unbound Medicine ER -