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One‐Pot Tandem Michael Addition/Enantioselective Conia‐Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis
Author(s) -
Horibe Takahiro,
Sakakibara Masato,
Hiramatsu Rin,
Takeda Kazuki,
Ishihara Kazuaki
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007180
Subject(s) - enantioselective synthesis , chemistry , tandem , catalysis , ene reaction , yield (engineering) , michael reaction , methylene , alkyl , proline , organic chemistry , organocatalysis , combinatorial chemistry , medicinal chemistry , amino acid , materials science , biochemistry , metallurgy , composite material
Abstract The first one‐pot tandem Michael addition/enantioselective Conia‐ene cyclization of N‐protected prop‐2‐yn‐1‐amines with 2‐methylene‐3‐oxoalkanoates promoted by chiral iron(III)/silver(I) cooperative catalysts has been developed. Alkyl 4‐methylenepyrrolidine‐3‐acyl‐3‐carboxylates, which can be transformed into β‐proline derivatives, are obtained in high yield with high enantioselectivity.