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Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition/Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro‐Dihydropyranone from Benzylidene Meldrum's Acid
Author(s) -
Toffano Martial,
Guillot Régis,
Bournaud Chloée,
Brière JeanFrançois,
VoThanh Giang
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100559
Subject(s) - chemistry , enantioselective synthesis , kinetic resolution , cycloaddition , catalysis , domino , tandem , stereochemistry , cascade reaction , ketone , selectivity , combinatorial chemistry , meldrum's acid , organic chemistry , materials science , composite material
A catalytic enantioselective vinylogous domino reaction has been achieved from ketone‐derived benzylidene Meldrum's acid and α‐ketolactones to provide spirolactone dihydropyranones with more than 99% ee. An Auto Tandem Catalysis (ATC) process resulting from dual and complementary role of (DHQ) 2 PHAL organocatalyst resulted in a sequence involving an asymmetric vinylogous formal (4+2) cycloaddition of benzylidene and the subsequent kinetic resolution operating through a 1,3‐prototropic shift leading to good yields (>50%) and the high selectivity.