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Highly Diastereo‐ and Enantioselective Michael Addition of Nitroalkanes to 2‐Enoyl‐Pyridine N ‐Oxides Catalyzed by Scandium(III)/Copper(II) Complexes
Author(s) -
Li Lijun,
Zhang Sheng,
Hu Yanbin,
Li Yanan,
Li Chong,
Zha Zhenggen,
Wang Zhiyong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502129
Subject(s) - pyridine , schiff base , catalysis , chemistry , enantioselective synthesis , michael reaction , ligand (biochemistry) , adduct , scandium , copper , polymer chemistry , medicinal chemistry , combinatorial chemistry , base (topology) , organic chemistry , receptor , mathematical analysis , biochemistry , mathematics
A C 2 ‐symmetric Schiff‐base ligand, derived from tridentate‐Schiff‐base, was developed and successfully applied to the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N ‐oxides. With this newly catalytic system, an unprecedented diastereoselectivity was obtained in the asymmetric Michael addition of nitroalkanes to 2‐enoyl‐pyridine N ‐oxides. In addition, a switch in enantioselectivity was achieved by using this newly catalytic system and our previous catalyst. After a facile reduction, the optically active adduct was converted to a biologically active dihydro ‐ 2 H ‐pyrrol 4 a . Furthermore, a connection of two tridentate‐Schiff‐base subunits proved to be an effective strategy in ligand design.