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Highly Enantioselective Tandem Michael Addition of Tryptamine‐Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids
Author(s) -
He Weigang,
Hu Jiadong,
Wang Pengyan,
Chen Le,
Ji Kai,
Yang Siyu,
Li Yin,
Xie Zhilong,
Xie Weiqing
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.201800567
Subject(s) - enantioselective synthesis , tryptamine , oxindole , pyrrolidine , chemistry , isatin , strychnos , indole test , tandem , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , alkaloid , materials science , biochemistry , composite material
A highly enantioselective tandem Michael addition of tryptamine‐derived oxindoles to alkynones was developed by taking advantage of a chiral N , N′ ‐dioxide Sc(OTf) 3 catalyst. The reaction enables the facile preparation of enantioenriched spiro[pyrrolidine‐3,3′‐oxindole] compounds, which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(−)‐tubifoline, (−)‐tubifolidine, (−)‐dehydrotubifoline] was achieved in 10–11 steps.