Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition / Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro‐Dihydropyranone from Benzylidene Meldrum’s Acid - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2021

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

Résumé

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)2PHAL 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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Dates et versions

hal-03304167 , version 1 (23-08-2021)

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Martial Toffano, Régis Guillot, Chloee Bournaud, Jean-François Brière, Giang Vo-Thanh. Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition / Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro‐Dihydropyranone from Benzylidene Meldrum’s Acid. Advanced Synthesis and Catalysis, 2021, 363, pp.4452-4458. ⟨10.1002/adsc.202100559⟩. ⟨hal-03304167⟩
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