Exploitation of the Arndt–Eistert Homologation of N-Methyl-α-Amino Acids for Concomitant Ester and N-Methyl Peptide Formation

Andrew B. Hughes; Brad E. Sleebs

doi:10.1071/CH07371

RESEARCH ARTICLE

Previous Next Contents Vol 61(2)

Exploitation of the Arndt–Eistert Homologation of N-Methyl-α-Amino Acids for Concomitant Ester and N-Methyl Peptide Formation

Andrew B. Hughes ^A ^C and Brad E. Sleebs ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, La Trobe University, Vic. 3086, Australia.

^B Current address: Medicinal Chemistry Group, Structural Biology Division, The Walter and Eliza Hall Institute of Medical Research, Vic. 3086, Australia.

^C Corresponding author. Email: a.hughes@latrobe.edu.au

Australian Journal of Chemistry 61(2) 131-137 https://doi.org/10.1071/CH07371
Submitted: 23 October 2007 Accepted: 17 January 2008 Published: 11 February 2008

Abstract

Results from studies of the Arndt–Eistert homologation of N-methyl-α-amino acids with concomitant ester and amide formation is discussed. The applicability of the use of ultrasound was investigated in the Wolff rearrangement of diazoketones for the production of esters and amides. This methodology was then applied to a novel ‘N-methyl coupling’ that allows simultaneous β-amino acid formation. Conventional ‘PyBroP N-methyl couplings’ were also performed as a comparison to establish the validity of the method.

Acknowledgement

The authors thank La Trobe University for scholarship funding of BES.

References

Exploitation of the Arndt–Eistert Homologation of N-Methyl-α-Amino Acids for Concomitant Ester and N-Methyl Peptide Formation

Abstract

Acknowledgement

Subscriber Login