Conjugate Additions of Amines to Maleimides via Cooperative Catalysis

A cooperative system comprising of a lithium Lewis acid and amine base significantly enhances the rate of the conjugate addition of a wide array of amines to maleimides. This operationally simple, scalable method provides mono‐addition products in high yields and purity. This conjugation was success...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 360; no. 8; pp. 1719 - 1725
Main Authors Uno, Brice E., Deibler, Kristine K., Villa, Carlos, Raghuraman, Arjun, Scheidt, Karl A.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 17.04.2018
Wiley Subscription Services, Inc
Subjects
Amines
amino-conjugate addition
bioconjugation
Catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Conjugation
cooperative catalysis
crizotinib
Fluorescent indicators
Lewis acid
Lithium
maleimide
Physical Sciences
Science & Technology
synergistic catalysis
ANNULATIONS
amino-conjugate addition
synergistic catalysis
LITHIUM AMIDES
AZA-MICHAEL ADDITION
NATURAL-PRODUCTS
cooperative catalysis
bioconjugation
crizotinib
maleimide
ACTIVATION STRATEGY
FLUORESCENCE
CHROMOPHORES
BINDING-SITE
STEREOSELECTIVE-SYNTHESIS
PROBE
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Summary:A cooperative system comprising of a lithium Lewis acid and amine base significantly enhances the rate of the conjugate addition of a wide array of amines to maleimides. This operationally simple, scalable method provides mono‐addition products in high yields and purity. This conjugation was successfully applied to the kinase inhibitor crizotinib in a chemoselective ligation to create novel fluorescent probe.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800160