"Chiral Building Blocks Based on 1,2-Disubstituted Diamantanes"

Andrey A. Fokin: Alexander E. Pashenko, Vladyslav V. Bakhonsky, Tatyana S. Zhuk, Lesya V. Chernish, Pavel A. Gunchenko, Andrey O. Kushko, Jonathan Becker, Raffael C. Wende, Peter R. Schreiner; Synthesis, 01/02/17.

Additional Authors: Alexander E. Pashenko, Vladyslav V. Bakhonsky, Tatyana S. Zhuk, Lesya V. Chernish, Pavel A. Gunchenko, Andrey O. Kushko, Jonathan Becker, Raffael C. Wende, Peter R. Schreiner

Abstract:

The reaction of 1-hydroxydiamantane with elemental bromine leads to consecutive cage opening and re-closure, thereby providing a straightforward approach to the class of previously unknown 1,2- disubstituted diamondoid derivatives. Functional group exchange gave, among others, chiral bidentate ligands 1,2-dihydroxy- and 1,2-diaminodiamantane. The latter was enantioseparated on gram scale with ee >98% through a single crystallization with (+)-tartaric acid.