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Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides
Authors:Dong Zhang  Prof. Dr. Lili Lin  Jian Yang  Prof. Dr. Xiaohua Liu  Prof. Dr. Xiaoming Feng
Affiliation:Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China
Abstract:A highly enantioselective synthesis of tetrahydroindolizines by catalytic multicomponent cycloaddition reactions of diazoacetate, pyridine, and alkenyloxindole was developed. Under the relay catalysis, involving an achiral iron(III) catalyst and chiral N,N′‐dioxide‐scandium(III) complex, a series of tetrahydroindolizines bearing different substituents were obtained in moderate to high yields (up to 99 %) with excellent diastereo‐ and enantioselectivities (up to >19:1 d.r., 99 % ee).
Keywords:asymmetric catalysis  heterocycles  iron  multicomponent reactions  scandium
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