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Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides
Author(s) -
Zhang Dong,
Lin Lili,
Yang Jian,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806630
Subject(s) - scandium , enantioselective synthesis , bimetallic strip , cycloaddition , catalysis , pyridinium , chemistry , pyridine , medicinal chemistry , combinatorial chemistry , organic chemistry
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 ).