Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition/Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro‐Dihydropyranone from Benzylidene Meldrum's Acid | Zendy

Toffano Martial | Zendy; Guillot Régis | Zendy; Bournaud Chloée | Zendy; Brière JeanFrançois | Zendy; VoThanh Giang | Zendy

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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 , stereochemistry , tandem , domino , cascade reaction , ketone , meldrum's acid , selectivity , combinatorial chemistry , 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.

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