Stereoselective synthesis of highly functionalized (Z)-chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid?

Chemical Communications Pub Date: 2021-06-09 DOI: 10.1039/D1CC02952E

Abstract

Described here is the first stereoselective synthesis of highly functionalized chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid (ααAA). This synthesis requires the construction of a quaternary carbon center, and this challenge was overcome by the Aza-Darzens condensation of ketimine with α,α-dichloroenolate, producing 2-chloroaziridines with quaternary carbon centers including spirocyclic motifs, which are valuable for the previously elusive synthesis of various ααAA-containing chloroalkene isosteres.

Graphical abstract: Stereoselective synthesis of highly functionalized (Z)-chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid
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