Nickel‐Catalyzed CO 2  Rearrangement of Enol Metal Carbonates for the Efficient Synthesis of β‐Ketocarboxylic Acids | Zendy

Ninokata Ryo | Zendy; Yamahira Tatsuya | Zendy; Onodera Gen | Zendy; Kimura Masanari | Zendy

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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

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 .

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