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Asymmetric Catalytic Reductive Coupling of 1,3‐Enynes and Aromatic Aldehydes
Author(s) -
Miller Karen M.,
Colby Elizabeth A.,
Woodin Katrina S.,
Jamison Timothy F.
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505175
Subject(s) - chemistry , regioselectivity , catalysis , trimethylsilyl , conjugated system , phosphine , denticity , combinatorial chemistry , ligand (biochemistry) , organic chemistry , medicinal chemistry , biochemistry , receptor , crystal structure , polymer
Nickel‐catalyzed reductive coupling reactions of 1,3‐enynes and aromatic aldehydes efficiently afford conjugated dienols in excellent regioselectivity and modest enantioselectivity when conducted in the presence of catalytic amounts of a monodentate, P ‐chiral ferrocenyl phosphine ligand. 1‐(Trimethylsilyl)‐substituted enynes are shown to be effective coupling partners in these reactions, and the dienol products thus formed readily undergo protiodesilylation under mild conditions.