Premium
Asymmetric Triple Relay Catalysis: Enantioselective Synthesis of Spirocyclic Indolines through a One‐Pot Process Featuring an Asymmetric 6π Electrocyclization
Author(s) -
Yin XiaoPing,
Zeng XingPing,
Liu YunLin,
Liao FuMin,
Yu JinSheng,
Zhou Feng,
Zhou Jian
Publication year - 2014
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.201407677
Subject(s) - enantioselective synthesis , catalysis , brønsted–lowry acid–base theory , chemistry , bifunctional , combinatorial chemistry , yield (engineering) , triple bond , isatin , bifunctional catalyst , aryl , organic chemistry , materials science , double bond , alkyl , metallurgy
A rare example of a one‐pot process that involves asymmetric triple relay catalysis is reported. The key step is an asymmetric [1,5] electrocyclic reaction of functionalized ketimines. The substrates for this process were obtained in situ in a two‐step process that involved the hydrogenation of nitroarenes with a Pd/C catalyst to yield aryl amines and their subsequent coupling with isatin derivatives in a Brønsted acid catalyzed ketimine formation reaction. The electrocyclization was catalyzed by a bifunctional chiral Brønsted base/hydrogen bond donor catalyst. The one‐pot process gave the desired products in good yields and with excellent enantioselectivity.