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Nickel‐Catalyzed CO 2 Rearrangement of Enol Metal Carbonates for the Efficient Synthesis of β‐Ketocarboxylic Acids
Author(s) -
Ninokata Ryo,
Yamahira Tatsuya,
Onodera Gen,
Kimura Masanari
Publication year - 2017
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.201609338
Subject(s) - enol , chemistry , catalysis , stereoselectivity , medicinal chemistry , nickel , metal , methylene , carbonate , oxidative coupling of methane , oxidative addition , photochemistry , organic chemistry
Abstract 4‐Methylene‐1,3‐dioxolan‐2‐ones underwent oxidative addition of a Ni 0 catalyst in the presence of Me 2 Al(OMe), followed by a coupling reaction with alkynes, to form δ,ϵ‐unsaturated β‐ketocarboxylic acids with high regio‐ and stereoselectivity. The reaction proceeds by [1,3] rearrangement of an enol metal carbonate intermediate and the formal reinsertion of CO 2 .