Chiral Building Blocks Based on 1,2-Disubstituted Diamantanes

SYNTHESIS-STUTTGART(2017)

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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.
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Key words
cage hydrocarbons,cyclization,diamondoids,fragmentation,halogenation
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