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Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates
Author(s) -
Zhuo ChunXiang,
Zhou Yong,
Cheng Qiang,
Huang Lin,
You ShuLi
Publication year - 2015
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.201507193
Subject(s) - stereocenter , tryptamine , enantioselective synthesis , chemistry , derivative (finance) , indole test , allylic rearrangement , stereochemistry , yield (engineering) , mannich reaction , combinatorial chemistry , catalysis , organic chemistry , materials science , biochemistry , financial economics , economics , metallurgy
The highly efficient synthesis of the enantioenriched spiroindolines by iridium‐catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo‐ and enantioselectivity. In addition, a chiral tryptamine derivative could be easily accessed in good yield with excellent ee value through an unprecedented dearomatization/retro‐Mannich/hydrolysis cascade reaction of an indole derivative.