Development of Zn-ProPhenol-Catalyzed Asymmetric Alkyne Addition: Synthesis of Chiral Propargylic Alcohols

作者:Trost Barry M*; Bartlett Mark J; Weiss Andrew H; Jacobi von Wangelin Axel; Chan Vincent S
来源:Chemistry - A European Journal, 2012, 18(51): 16498-16509.
DOI:10.1002/chem.201202085

摘要

The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and a,beta-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products.

  • 出版日期2012-12