Synthesis of Novel Planar-Chiral Charge-Compensated nido-Carborane-Based Amino Acid.

ABSTRACT: Amino acids with unusual types of chirality and their derivatives have recently attracted attention as precursors in the synthesis of chiral catalysts and peptide analogues with unique properties. In this study, we have synthesized a new nido-carborane-based planar-chiral amino acid, in the molecule of which the amino group is directly bonded to the B(3) atom, and the carboxyl group is attached to the B(9) atom through the CH₂S⁺(Me) fragment. 3-Amino-9-dimethylsulfonio-nido-carborane, prepared in three steps from 3-amino-closo-carborane in a high yield, was a key intermediate in the synthesis of the target planar-chiral amino acid. The carboxymethyl group at the sulfur atom was introduced by the demethylation reaction of the dimethylsulfonio deriv

SUBMITTER: Gruzdev DA 

PROVIDER: S-EPMC11434195 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature