Auto Tandem Catalysis: Asymmetric Vinylogous Cycloaddition/Kinetic Resolution Sequence for the Enantioselective Synthesis of Spiro-Dihydropyranone from Benzylidene Meldrum's Acid,Advanced Synthesis & Catalysis

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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
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-07-27 , DOI: 10.1002/adsc.202100559
martial TOFFANO ₁ , Régis Guillot ₂ , Chloee BOURNAUD ₂ , jean-François Brière ₃ , Giang Vo-Thanh ₂

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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.

中文翻译：

自动串联催化：从亚苄基 Meldrum 酸对映选择性合成螺二氢吡喃酮的不对称乙烯基环加成/动力学拆分序列

已经从酮衍生的亚苄基 Meldrum 酸和 α-酮内酯实现了催化对映选择性乙烯基多米诺反应，以提供具有超过 99% ee 的螺内酯二氢吡喃酮。由 (DHQ) ₂ PHAL 有机催化剂的双重和互补作用产生的自动串联催化 (ATC) 过程产生了一个序列，涉及亚苄基的不对称乙烯基形式 (4+2) 环加成和随后通过 1,3- 操作的动力学拆分质子转移导致良好的产率（> 50％）和高选择性。

更新日期：2021-09-21

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