Premium
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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202014489
Subject(s) - synthon , organocatalysis , chemistry , cycloaddition , dihydropyran , meldrum's acid , catalysis , ketone , brønsted–lowry acid–base theory , organic chemistry , decane , combinatorial chemistry , 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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom