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- W4214678613 abstract "Abstract The enantioselective aza‐Diels–Alder reaction is efficient for constructing chiral tetrahydropyridines, but the catalytic asymmetric aza‐Diels–Alder reaction of ketimines with unactivated dienes is still a challenging topic. Herein, guided by computational screening, a highly enantioselective aza‐Diels–Alder reaction of 2‐aryl‐3 H ‐indol‐3‐ones with unactivated dienes was realized by using a B(C 6 F 5 ) 3 /chiral phosphoric acid catalyst system under mild conditions. The reaction has a broad scope with respect to both aza‐Diels–Alder reaction partners and hence offers rapid access to an array of tetrahydropyridine derivatives with pretty outcomes (up to 99 % yield, >20:1 dr and 98:2 er). The reaction is very efficient: lowering catalyst loadings for the model reaction to 0.1 mol %, enantioselectivity is still maintained. The synthetic utility was confirmed by transformations of the products. DFT calculations provide convincing evidence for the interpretation of stereoselection." @default.
- W4214678613 created "2022-03-02" @default.
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- W4214678613 date "2021-06-30" @default.
- W4214678613 modified "2023-10-16" @default.
- W4214678613 title "Catalytic Asymmetric Aza‐Diels–Alder Reaction of Ketimines and Unactivated Dienes" @default.
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- W4214678613 doi "https://doi.org/10.1002/ange.202104788" @default.
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