Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and α-Hydroxy Ketones
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- 1 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (12) , 3442-3443
- https://doi.org/10.1021/ja034366y
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 α-hydroxy ketone synthesis.Keywords
This publication has 14 references indexed in Scilit:
- Catalytic Three‐Component Coupling of Alkynes, Imines, and Organoboron ReagentsAngewandte Chemie International Edition in English, 2003
- P-Chiral, Monodentate Ferrocenyl Phosphines, Novel Ligands for Asymmetric CatalysisThe Journal of Organic Chemistry, 2002
- Platinum-Catalyzed Enantioselective Aldol Addition of Ketene Silyl Acetals to AldehydesJournal of the American Chemical Society, 1998
- A New Stereoselective Method for the Preparation of Allylic AlcoholsJournal of the American Chemical Society, 1997
- Substrate-directable chemical reactionsChemical Reviews, 1993
- Asymmetric hydroxylation of enolates with N-sulfonyloxaziridinesChemical Reviews, 1992
- Acutiphycin and 20,21-didehydroacutiphycin, new antineoplastic agents from the cyanophyte Oscillatoria acutissimaJournal of the American Chemical Society, 1984
- Tritium labeling of organic compounds by HNaY zeolite catalyzed exchange with tritiated water and their analysis by tritium NMRJournal of the American Chemical Society, 1981
- Total synthesis of 6-deoxyerythronolide BJournal of the American Chemical Society, 1981
- 3,4-Pyridyne and its dimerJournal of the American Chemical Society, 1971