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Asymmetric Catalytic Double Michael Additions for the Synthesis of Spirooxindoles
Author(s) -
Kang Tengfei,
Zhao Peng,
Yang Jian,
Lin Lili,
Feng Xiaoming,
Liu Xiaohua
Publication year - 2018
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.201800043
Subject(s) - pyrrolidine , michael reaction , chemistry , guanidine , catalysis , enantioselective synthesis , organocatalysis , organic chemistry , combinatorial chemistry
Asymmetric cascade double Michael additions to construct 2′‐substituted 3,3′‐spirooxindoles by using a chiral guanidine organocatalyst has been developed. A series of spirooxindole derivatives containing dihydrofuran or pyrrolidine subunits were obtained with good to excellent diastereo‐ and enantioselectivities. The method showed great tolerance of a number of aromatic and aliphatic alkynones. The strategy gave access to the asymmetric synthesis of (−)‐salacin for the first time.