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Abstract
An efficient inverse electron-demand aza-Diels-Alder reaction of different types of olefins and 1,2-diaza-1,3-dienes, which could be readily formed in situ from α-halogeno hydrazones and a base, has been successfully developed. With the developed approach, a wide range of fused polycyclic tetrahydropyridazines were smoothly obtained in up to 95% yield and ee up to 98% with dr >20:1 under optimal reaction conditions. A gram-scale experiment and further derivatizations of the polycyclic tetrahydropyridazine products were also conducted to verify the practicability of the methodology.
Supplementary materials
Title
Catalytic Asymmetric Synthesis of Fused Polycyclic Tetrahydropyridazine through Inverse‐Electron‐Demand Aza-Diels-Alder Reaction of Olefins with Azoalkenes in Situ Generated from α‑Halogeno Hydrazones
Description
An efficient inverse electron-demand aza-Diels-Alder reaction of different types of olefins and 1,2-diaza-1,3-dienes, which could be readily formed in situ from α-halogeno hydrazones and a base, has been successfully developed. With the developed approach, a wide range of fused polycyclic tetrahydropyridazines were smoothly obtained in up to 95% yield and ee up to 98% with dr >20:1 under optimal reaction conditions. A gram-scale experiment and further derivatizations of the polycyclic tetrahydropyridazine products were also conducted to verify the practicability of the methodology.
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