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Chiral Lewis Acid Catalyzed Reactions of α‐Diazoester Derivatives: Construction of Dimeric Polycyclic Compounds
Author(s) -
Tan Fei,
Liu Xiaohua,
Wang Yan,
Dong Shunxi,
Yu Han,
Feng Xiaoming
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.201810030
Subject(s) - chemistry , catalysis , cycloaddition , intermolecular force , lewis acids and bases , isatin , combinatorial chemistry , stereochemistry , organic chemistry , molecule
An unexpected homologation/dyotropic rearrangement/interconversion/[3+2] cycloaddition cascade reaction of α‐diazoester‐terminated N‐propyl‐substituted isatin derivatives was achieved in the presence of a chiral N,N′‐dioxide/Sc III catalyst. This catalytic manifold allows rapid construction of several classes of dimeric polycyclic compounds with good yields and high levels of diastereo‐ and enantioselectivity (up to 99 % ee ). Furthermore, macrocyclic dimers can be obtained by an intermolecular homologation process.