(7,8-Dicarba-nido-undecaboran-7-yl)acetic acid: synthesis of individual enantiomers and the first example of the determination of the absolute configuration of chiral monosubstituted nido-carborane

Abstract

Individual (RP)- and (SP)-enantiomers of planar-chiral (7,8-dicarba-nido-undecaboran-7-yl)acetic acid were obtained for the first time by deboronation of the derivatives of achiral (1,2-dicarba-closo-dodecaboran-1-yl)acetic acid containing residues of natural amino acids and...

Catalytic asymmetric synthesis of carboranylated diols bearing two adjacent stereocenters located at the α,β-position ofo-carborane cage carbon

“…After reduction of azide compound 8 and acidification, the final nido -carboranyl derivatives of chiral amino alcohol 9 were obtained in the form of zwitterions. It is noteworthy that a new planar chirality of the boron cage was generated from the deboronation reaction, 20 meaning that nido -carborane species 8 and 9 have three chirality elements in total. The introduction of a negatively charged nido -carborane group makes it possible to obtain novel zwitterionic lipophilic nido -carborane-containing chiral amino alcohol derivatives.…”

Synthesis of Charge-Compensated nido-Carboranyl Derivatives of Sulfur-Containing Amino Acids and Biotin

“…In this regard, the development of synthetic approaches to new carboranyl derivatives of amino acids is of considerable interest. Previously, we have obtained a series of carboranyl derivatives of natural amino acids containing a 3-amino- closo - o -carborane residue as well as planar-chiral closo - and nido -carborane-based amino acids …”