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- W3011427648 abstract "A highly chemoselective and enantioselective cyclization of γ-chloroenals and ketimines has been developed to synthesize enantiopure 3,4-2H-pyrindin-2-ones as major products. It is proposed that the intermediate enone IV reacted with an enamine to proceed with a [3 + 3] cyclization, thereby affording 3,4-2H-pyrindin-2-ones as major products. Interestingly, the addition of LiCl promoted the formation of the enamine and accelerated the [3 + 3] cyclization. In contrast, the [4 + 2] cycloaddition reaction between the intermediate vinyl enolate VIII and an imine offered 5,6-2H-pyrindin-2-ones as minor products. This protocol represents the exceptional potential of N-heterocyclic carbene (NHC) catalytic reactions in accessing biologically active 3,4-2H-pyrindin-2-one derivatives in good yield with high chemoselectivities and excellent enantiomeric purities." @default.
- W3011427648 created "2020-03-23" @default.
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- W3011427648 date "2020-03-11" @default.
- W3011427648 modified "2023-10-17" @default.
- W3011427648 title "Highly Chemoselective and Enantioselective Synthesis of 3,4-2<i>H</i>-Pyrindin-2-ones by an NHC-Catalyzed [3 + 3] Cyclization" @default.
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- W3011427648 doi "https://doi.org/10.1021/acs.orglett.0c00699" @default.
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