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Switch of Selectivity in the Synthesis of α‐Methylene‐γ‐Lactones: Palladium‐Catalyzed Intermolecular Carboesterification of Alkenes with Alkynes
Author(s) -
Huang Liangbin,
Wang Qian,
Liu Xiaohang,
Jiang Huanfeng
Publication year - 2012
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.201109141
Subject(s) - alkene , alkyne , methylene , stereoselectivity , chemistry , domino , catalysis , intermolecular force , palladium , combinatorial chemistry , selectivity , organic chemistry , molecule
Three in one : A highly efficient and mild Pd II ‐catalyzed carboesterification of alkenes with carboxylic alkyne derivatives proceeds through a domino‐type alkyne–alkene coupling/CO‐bond formation (see scheme). The stereoselectivity is controlled by the choice of substrates and temperature. The reaction provides a convenient method for the construction of naturally occurring biologically active compounds with α‐methylene‐γ‐lactone skeletons.