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

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 o...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-07, Vol.57 (56), p.6915-6918
Main Authors: Kodama, Yuki, Imai, Saki, Fujimoto, Junko, Sato, Kohei, Mase, Nobuyuki, Narumi, Tetsuo
Format: Article
Language:English
Subjects:
Amino acids
Carbon
Crystallography
Stereoselectivity
Synthesis
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Summary: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. Stereoselective synthesis of ( Z )-chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid was realized from structurally unique tetra-substituted spirocyclic aziridines.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc02952e