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Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones
Author(s) -
Wittmann Stéphane,
Martzel Thomas,
Pham Truong Cong Thanh,
Toffano Martial,
Oudeyer Sylvain,
Guillot Régis,
Bournaud Chloée,
Gandon Vincent,
Brière JeanFrançois,
VoThanh Giang
Publication year - 2021
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.202014489
Subject(s) - synthon , chemistry , dihydropyran , organocatalysis , cycloaddition , catalysis , ketone , decane , organic chemistry , meldrum's acid , brønsted–lowry acid–base theory , enantioselective synthesis
Upon Brønsted base organocatalysis, ketone‐derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro‐2,3‐furandione, providing an unprecedented route to 3,6‐dihydropyran‐2‐ones as spiro[4.5]decane derivatives with up to 98 % ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones, establishing these alkylidene Meldrum's acids as a novel C4‐synthon in the vinylogous series.
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