Copper/Guanidine-Catalyzed Asymmetric Alkynylation of Isatins

The highly enantioselective alkynylation of isatins, catalyzed by a bifunctional guanidine/CuI catalyst under mild reaction conditions, is described. The reaction is broad in scope with respect to alkyl/aryl‐substituted terminal alkynes and substituted isatins, thus affording bioactive propargylic a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-04, Vol.55 (17), p.5286-5289
Main Authors: Chen, Quangang, Tang, Yu, Huang, Tianyu, Liu, Xiaohua, Lin, Lili, Feng, Xiaoming
Format: Article
Language:English
Subjects:
Alcohols
Alkynes
Aromatic compounds
asymmetric catalysis
Biocompatibility
Catalysts
copper
Enantiomers
Guanidine
heterocycles
ligand design
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Summary:The highly enantioselective alkynylation of isatins, catalyzed by a bifunctional guanidine/CuI catalyst under mild reaction conditions, is described. The reaction is broad in scope with respect to alkyl/aryl‐substituted terminal alkynes and substituted isatins, thus affording bioactive propargylic alcohols in excellent yields and enantioselectivities. Active duty: Asymmetric alkynylation of isatins was achieved by a new bifunctional chiral guanidine ligand in combination with CuI under mild reaction conditions. Good levels of reactivity and excellent enantioselectivities were achieved with diverse alkyl‐ and aryl‐substituted terminal alkynes and various substituted isatins, thus generating bioactive 3‐alkynyl‐3‐hydroxyindolin‐2‐ones.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201600711