Tantalum pentachloride as a coupling agent for stereohindered amide bond formation

Jiang Bao Fang; Rashmi Sanghi; Joachim Kohn; Alan S. Goldman

doi:10.1016/j.ica.2004.03.007

Tantalum pentachloride as a coupling agent for stereohindered amide bond formation

Jiang Bao Fang, Rashmi Sanghi, Joachim Kohn, Alan S. Goldman

Rutgers University

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

9 Citations (Scopus)

Abstract

We have previously reported that tantalum carboxylates show high reactivity toward primary amines to give primary amides. We report herein that tantalum pentachloride, in contrast with the behavior of standard coupling reagents, mediates the couplings of secondary amines and the couplings of very hindered carboxylates. Such coupling reactions are particularly difficult to achieve, when using chiral carboxylates (including N-protected amino acids), without a significant degree of accompanying racemization. Racemization levels with the present systems are found to be very low in comparison with those obtained using a standard amide/peptide coupling system (DCC/HOBt).

Original language	English
Pages (from-to)	2415-2426
Number of pages	12
Journal	Inorganica Chimica Acta
Volume	357
Issue number	9
DOIs	https://doi.org/10.1016/j.ica.2004.03.007
Publication status	Published - Jul 5 2004

Keywords

Amide
Carboxylato
Coupling
Peptide
Tantalum

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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title = "Tantalum pentachloride as a coupling agent for stereohindered amide bond formation",

abstract = "We have previously reported that tantalum carboxylates show high reactivity toward primary amines to give primary amides. We report herein that tantalum pentachloride, in contrast with the behavior of standard coupling reagents, mediates the couplings of secondary amines and the couplings of very hindered carboxylates. Such coupling reactions are particularly difficult to achieve, when using chiral carboxylates (including N-protected amino acids), without a significant degree of accompanying racemization. Racemization levels with the present systems are found to be very low in comparison with those obtained using a standard amide/peptide coupling system (DCC/HOBt).",

keywords = "Amide, Carboxylato, Coupling, Peptide, Tantalum",

author = "Fang, {Jiang Bao} and Rashmi Sanghi and Joachim Kohn and Goldman, {Alan S.}",

note = "Funding Information: Support from the National Science Foundation (Grant CHE-9704304 to A.S.G.) and from the New Jersey Center for Biomaterials is gratefully acknowledged. Louis Whaley (Rutgers University) is thanked for very helpful discussions.",

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doi = "10.1016/j.ica.2004.03.007",

language = "English",

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journal = "Inorganica Chimica Acta",

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T1 - Tantalum pentachloride as a coupling agent for stereohindered amide bond formation

AU - Fang, Jiang Bao

AU - Sanghi, Rashmi

AU - Kohn, Joachim

AU - Goldman, Alan S.

N1 - Funding Information: Support from the National Science Foundation (Grant CHE-9704304 to A.S.G.) and from the New Jersey Center for Biomaterials is gratefully acknowledged. Louis Whaley (Rutgers University) is thanked for very helpful discussions.

PY - 2004/7/5

Y1 - 2004/7/5

N2 - We have previously reported that tantalum carboxylates show high reactivity toward primary amines to give primary amides. We report herein that tantalum pentachloride, in contrast with the behavior of standard coupling reagents, mediates the couplings of secondary amines and the couplings of very hindered carboxylates. Such coupling reactions are particularly difficult to achieve, when using chiral carboxylates (including N-protected amino acids), without a significant degree of accompanying racemization. Racemization levels with the present systems are found to be very low in comparison with those obtained using a standard amide/peptide coupling system (DCC/HOBt).

AB - We have previously reported that tantalum carboxylates show high reactivity toward primary amines to give primary amides. We report herein that tantalum pentachloride, in contrast with the behavior of standard coupling reagents, mediates the couplings of secondary amines and the couplings of very hindered carboxylates. Such coupling reactions are particularly difficult to achieve, when using chiral carboxylates (including N-protected amino acids), without a significant degree of accompanying racemization. Racemization levels with the present systems are found to be very low in comparison with those obtained using a standard amide/peptide coupling system (DCC/HOBt).

KW - Amide

KW - Carboxylato

KW - Coupling

KW - Peptide

KW - Tantalum

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JO - Inorganica Chimica Acta

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ER -

Tantalum pentachloride as a coupling agent for stereohindered amide bond formation

Abstract

Keywords

ASJC Scopus subject areas

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