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 | |
| Publication status | Published - Jul 5 2004 |
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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 journal › Article
}
TY - JOUR
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
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
UR - http://www.scopus.com/inward/record.url?scp=3042572505&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=3042572505&partnerID=8YFLogxK
U2 - 10.1016/j.ica.2004.03.007
DO - 10.1016/j.ica.2004.03.007
M3 - Article
VL - 357
SP - 2415
EP - 2426
JO - Inorganica Chimica Acta
JF - Inorganica Chimica Acta
SN - 0020-1693
IS - 9
ER -