Tantalum pentachloride as a coupling agent for stereohindered amide bond formation

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

Research output: Contribution to journalArticle

8 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 languageEnglish
Pages (from-to)2415-2426
Number of pages12
JournalInorganica Chimica Acta
Volume357
Issue number9
DOIs
Publication statusPublished - Jul 5 2004

Fingerprint

Coupling agents
Tantalum
tantalum
Amides
amides
Amines
chlorides
carboxylates
Peptides
Amino acids
amines
Amino Acids
peptides
reagents
amino acids
reactivity
tantalum pentachloride
1-hydroxybenzotriazole

Keywords

  • Amide
  • Carboxylato
  • Coupling
  • Peptide
  • Tantalum

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Tantalum pentachloride as a coupling agent for stereohindered amide bond formation. / Fang, Jiang Bao; Sanghi, Rashmi; Kohn, Joachim; Goldman, Alan S.

In: Inorganica Chimica Acta, Vol. 357, No. 9, 05.07.2004, p. 2415-2426.

Research output: Contribution to journalArticle

Fang, Jiang Bao ; Sanghi, Rashmi ; Kohn, Joachim ; Goldman, Alan S. / Tantalum pentachloride as a coupling agent for stereohindered amide bond formation. In: Inorganica Chimica Acta. 2004 ; Vol. 357, No. 9. pp. 2415-2426.
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