Conjugate Additions of Amines to Maleimides via Cooperative Catalysis

Brice E. Uno; Kristine K. Deibler; Carlos Villa; Arjun Raghuraman; Karl A. Scheidt

doi:10.1002/adsc.201800160

Conjugate Additions of Amines to Maleimides via Cooperative Catalysis

Brice E. Uno, Kristine K. Deibler, Carlos Villa, Arjun Raghuraman, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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. (Figure presented.).

Original language	English (US)
Pages (from-to)	1719-1725
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	360
Issue number	8
DOIs	https://doi.org/10.1002/adsc.201800160
State	Published - Apr 17 2018

Keywords

amino-conjugate addition
bioconjugation
cooperative catalysis
crizotinib
maleimide
synergistic catalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201800160

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title = "Conjugate Additions of Amines to Maleimides via Cooperative Catalysis",

abstract = "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. (Figure presented.).",

keywords = "amino-conjugate addition, bioconjugation, cooperative catalysis, crizotinib, maleimide, synergistic catalysis",

author = "Uno, {Brice E.} and Deibler, {Kristine K.} and Carlos Villa and Arjun Raghuraman and Scheidt, {Karl A.}",

note = "Funding Information: Financial support for this work was generously provided by the DOW Chemical Company. Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Villa, Carlos

AU - Raghuraman, Arjun

AU - Scheidt, Karl A.

PY - 2018/4/17

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KW - amino-conjugate addition

KW - bioconjugation

KW - cooperative catalysis

KW - crizotinib

KW - maleimide

KW - synergistic catalysis

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Conjugate Additions of Amines to Maleimides via Cooperative Catalysis

Abstract

Keywords

ASJC Scopus subject areas

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