One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids

Iryna O. Lebedyeva; Suvendu Biswas; Kevin Goncalves; Sean M. Sileno; Ashton R. Jackson; Kunal Patel; Peter J. Steel; Alan R. Katritzky

doi:10.1002/chem.201403529

One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids

Iryna O. Lebedyeva, Suvendu Biswas, Kevin Goncalves, Sean M. Sileno, Ashton R. Jackson, Kunal Patel, Peter J. Steel, Alan R. Katritzky

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

6 Scopus citations

Abstract

Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.

Original language	English (US)
Pages (from-to)	11695-11698
Number of pages	4
Journal	Chemistry - A European Journal
Volume	20
Issue number	37
DOIs	https://doi.org/10.1002/chem.201403529
State	Published - Sep 8 2014

Keywords

acylation
cleavage reactions
conjugates
decarboxylation
peptides

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.201403529

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title = "One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids",

abstract = "Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.",

keywords = "acylation, cleavage reactions, conjugates, decarboxylation, peptides",

author = "Lebedyeva, {Iryna O.} and Suvendu Biswas and Kevin Goncalves and Sileno, {Sean M.} and Jackson, {Ashton R.} and Kunal Patel and Steel, {Peter J.} and Katritzky, {Alan R.}",

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T1 - One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids

AU - Lebedyeva, Iryna O.

AU - Biswas, Suvendu

AU - Goncalves, Kevin

AU - Sileno, Sean M.

AU - Jackson, Ashton R.

AU - Patel, Kunal

AU - Steel, Peter J.

AU - Katritzky, Alan R.

PY - 2014/9/8

Y1 - 2014/9/8

N2 - Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.

AB - Monocarbonyl activation of 2,2-disubstituted malonic acids with benzotriazole leads to decarboxylation of one of the carboxy groups and formation of a C-H bond. Intermediate carbonyl benzotriazoles then readily acylate nucleophilic reagents and peptides resulting in libraries of conjugates and peptidomimetics.

KW - acylation

KW - cleavage reactions

KW - conjugates

KW - decarboxylation

KW - peptides

UR - http://www.scopus.com/inward/record.url?scp=84906948375&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84906948375&partnerID=8YFLogxK

U2 - 10.1002/chem.201403529

DO - 10.1002/chem.201403529

M3 - Article

AN - SCOPUS:84906948375

SN - 0947-6539

VL - 20

SP - 11695

EP - 11698

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 37

ER -

One-pot decarboxylative acylation of N-, O-, S-nucleophiles and peptides with 2,2-disubstituted malonic acids

Abstract

Keywords

ASJC Scopus subject areas

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