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Updated: Jul 19, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis
Santos Fustero1, María Sanchez-Roselló, Juan F Sanz-Cervera
1Departamento de Química Organica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Abstract:
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
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