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. 2003 Oct 16;5(21):3887-90.
doi: 10.1021/ol0354730.

Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides

Marco Molteni  1 , Alessandro Volonterio, Matteo Zanda
Affiliations

Stereocontrolled synthesis of psi[CH(CF3)NH]gly-peptides

Marco Molteni et al. Org Lett. .

Abstract

[reaction: see text] A novel class of peptidomimetics having a stereogenic [CH(CF(3))NH] replacement for a [CONH] peptide bond has been synthesized. The new compounds have been obtained in a stereocontrolled fashion using a kinetically controlled aza-Michael addition of chiral alpha-amino acid esters to trans-3,3,3-trifluoro-1-nitropropene. The stereoselectivity is strongly influenced by the solvent, the base, its stoichiometry, and the R side-chain. Diastereomeric ratios higher than 11:1 were achieved using H-Val-OtBu.HCl in toluene with 1.1 equiv of DIPEA.

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