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Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine
Author(s) -
Guo Chang,
Song Jin,
Huang JianZhou,
Chen PengHao,
Luo ShiWei,
Gong LiuZhu
Publication year - 2012
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.201107079
Subject(s) - enantioselective synthesis , stereocenter , substitution (logic) , yield (engineering) , total synthesis , computer science , stereochemistry , chemistry , catalysis , organic chemistry , programming language , materials science , metallurgy
Something constructive : The title reaction involving 3‐hydroxyoxindoles gives 3,3′‐disubstituted oxindoles with concomitant generation of an all‐carbon quaternary stereogenic center in high yield and excellent enantioselectivity. This reaction enabled the enantioselective construction of hexahydropyrroloindole skeletons and the first catalytic enantioselective total synthesis of (+)‐folicanthine.