The Carbenoid Approach to Peptide Synthesis

14). Direct conversion, by using methyl diazophenylacetate, of amino acid amides to phenylglycine-containing dipeptides 19 proceeds in good chemical yield, but with poor diastereoselectivity. -->
ISSN: 1521-3765
0947-6539
DOI: 10.1002/1521-3765(20000616)6:12<2160::aid-chem2160>3.0.co;2-y
Přístupová URL adresa: https://explore.openaire.eu/search/publication?articleId=doi_________::568c33f7a0704f8e64001a6b4e943aaf
https://doi.org/10.1002/1521-3765(20000616)6:12<2160::aid-chem2160>3.0.co;2-y
Rights: CLOSED
Přírůstkové číslo: edsair.doi...........568c33f7a0704f8e64001a6b4e943aaf
Autor: Diane Mary Coe, Paul A. Clarke, Richard T. Buck, Neil D. Pearson, Leigh Ferris, Martin James Drysdale, David Haigh, Elizabeth Swann, Christopher J. Moody
Rok vydání: 2000
Předmět:
Zdroj: Chemistry - A European Journal. 6:2160-2167
ISSN: 1521-3765
0947-6539
DOI: 10.1002/1521-3765(20000616)6:12<2160::aid-chem2160>3.0.co;2-y
Popis: A different approach to the synthesis of dipeptides is described based on the formation of the NHCHR1CONH-CHR2CO bond by carbenoid N-H insertion, rather than the formation of the peptide bond itself. Thus decomposition of triethyl diazophosphonoacetate catalysed by rhodium(II) acetate in the presence of N-protected amino acid amides 8 gives the phosphonates 9. Subsequent Wadsworth-Emmons reaction of 9 with aldehydes in the presence of DBU gives dehydro dipeptides 10. The reaction has been extended to a simple two-step procedure, without the isolation of the intermediate phosphonate, for conversion of a range of amino acid amides 11 into dehydro dipeptides 12 and to an N-methylamide 11 h, and for conversion of a dipeptide to tripeptide (13-->14). Direct conversion, by using methyl diazophenylacetate, of amino acid amides to phenylglycine-containing dipeptides 19 proceeds in good chemical yield, but with poor diastereoselectivity.
Databáze: OpenAIRE
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