Beilstein J. Org. Chem.2017,13, 2428–2441, doi:10.3762/bjoc.13.240
substituents in the Cα-position facilitate a base induced rearrangementtoα,β-unsaturatedimines, while azide-substituted propargylamines form triazoles under surprisingly mild conditions. A panel of propargylamines bearing fluoro or chloro substituents, polar functional groups, or basic and acidic functional
groups is accessible for the use as precursors of peptidomimetics.
Keywords: amino acid analogous side chains; desilylation; Ellman’s chiral sulfinamide; intramolecular Huisgen reaction; peptidomimetics; propargylamines; rearrangementtoα,β-unsaturatedimines; Introduction
Terminal alkynes display an
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Graphical Abstract
Figure 1:
Concept of carboxylic acid or amide bond replacement on the basis of an alkyne moiety.