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DBU‐Catalyzed Regioselective α ‐Alkylation of Enones Using the Vinylogous Strategy
Author(s) -
Tian Yawei,
Shang Yaping,
Su Weiping
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100293
Subject(s) - chemistry , regioselectivity , alkylation , catalysis , acrylate , combinatorial chemistry , organic chemistry , stereochemistry , monomer , polymer
A convenient and atom‐economic transformation of enones with electron‐deficient alkenes under mild conditions has been developed using DBU as a catalyst. This method utilizes vinylogous strategy to form dienolate intermediates, which provides a new approach for the regioselective α‐alkylation of enones. This protocol exhibits a broad range of substrate scope and good functional group compatibility. Moreover, it enabled the formation of unexpected cyclic 1,5‐diketone by employing phenyl acrylate as Michael acceptor to construct all‐carbon quaternary centers at γ‐position of enones. Overall, this synthetic method establishes a new route from readily available enones to valuable 1,5‐dicarbonyl compounds.