Azopeptides: Synthesis and Pericyclic Chemistry

作者:Chingle Ramesh; Lubell William D*
来源:Organic Letters, 2015, 17(21): 5400-5403.
DOI:10.1021/acs.orglett.5b02723

摘要

Azopeptides possess an imino urea as an amino amide surrogate in the sequence. Azopeptides were synthesized by oxidation of aza-glycine residues and employed in pericyclic chemistry. Diels-Alder cyclizations and Alder-ene reactions on azopeptides enabled construction of constrained aza-pipecolyl and reactive aza-allylglycyl residues. X-ray crystallographic analyses of azopeptide 16a and azapeptides 30a and 35a provided insight into imino urea configuration and conformational affects of cycloalkane side chains at the semicarbazide alpha- and beta-nitrogen, respectively.

  • 出版日期2015-11-6