Synthesis of a novel planar-chiral nido-carborane amino acid

• Published in: Russian chemical bulletin Vol. 70; no. 3; pp. 539 - 544
• Main Authors: Telegina, A. A., Gruzdev, D. A., Levit, G. L., Krasnov, V. P.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-03-2021; Springer Nature B.V
• Subjects: Acetic acid; Amino acids; Carborane; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Enantiomers; Full Articles; Inorganic Chemistry; Organic Chemistry; planar chirality; carborane; amino acid; deboronation
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-021-3121-7

The deboronation of enantiomers of planar-chiral benzyl (3-formamido-1,2-dicarba-
closo
-dodecaboran-1-yl)acetate gave the individual (
R
P
)- and (
S
P
)-enantiomers (
ee
> 98%) of a new amino acid containing a
nido
-carborane fragment, (3-ammonio-7,8-dicarba-
nido
-undecaboran-7-yl)acetic acid. Chiral HPLC methods for the analysis of enantiomeric purity of this compound was developed.