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Nickel‐Catalyzed Cycloaddition of α,β,γ,δ‐Unsaturated Ketones with Alkynes
Author(s) -
Horie Hiroaki,
Kurahashi Takuya,
Matsubara Seijiro
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201104286
Subject(s) - stereoselectivity , nickel , cycloaddition , intramolecular force , chemistry , catalysis , bicyclic molecule , medicinal chemistry , organic chemistry
As easy as α, β, γ, δ : The title reaction unexpectedly resulted in the stereoselective synthesis of bicyclo[3.1.0]hexenes (see scheme). The high level of stereoselection is attributed to a mechanistic pathway involving the oxidative cyclization of nickel(0) with α,β,γ,δ‐unsaturated ketones and alkynes, and the subsequent intramolecular carbonickelation.