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Enantioselective Reductive Coupling of 1,3-Enynes to Glyoxalates Mediated by Hydrogen: Asymmetric Synthesis of β,γ-Unsaturated α-Hydroxy Esters
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Section:Abstract
Catalytic hydrogenation of 1,3-enynes 1a−8a in the presence of ethyl glyoxalate at ambient pressure and temperature using a rhodium catalyst modified by (R)-(3,5-tBu-4-MeOPh)-MeO-BIPHEP results in highly regio- and enantioselective reductive coupling to furnish the corresponding α-hydroxy esters 1b−8b. As demonstrated by the elaboration of α-hydroxy ester 1b, the terminal and internal olefin moieties embodied by the diene side chain are subject to selective manipulation, one over the other.
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This article has been cited by 17 ACS Journal articles (5 most recent appear below).
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Origins of Regioselectivity and Alkene-Directing Effects in Nickel-Catalyzed Reductive Couplings of Alkynes and Aldehydes
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- Published In Issue September 13, 2007
- Received July 2, 2007
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