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Development of Zn–ProPhenol‐Catalyzed Asymmetric Alkyne Addition: Synthesis of Chiral Propargylic Alcohols
Author(s) -
Trost Barry M.,
Bartlett Mark J.,
Weiss Andrew H.,
von Wangelin Axel Jacobi,
Chan Vincent S.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202085
Subject(s) - alkyne , dimethylzinc , enantioselective synthesis , chemistry , reagent , catalysis , zinc , combinatorial chemistry , aryl , organic chemistry , ligand (biochemistry) , yield (engineering) , materials science , biochemistry , alkyl , receptor , metallurgy
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 α,β‐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.