Elsevier

Tetrahedron Letters

Volume 32, Issue 14, 1 April 1991, Pages 1711-1714
Tetrahedron Letters

Preparation of trans-1,2-diamino-1,2-dimethylcyclohexane via highly stereoselective olefin oxidation by dinitrogen tetroxide

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Abstract

Reaction of N2O4 with 1,2-dimethylcyclohexene led to the corresponding dinitro compound 4 with high trans stereoselectivity (>30:1). Catalytic hydrogenation of 4 with Pd(OH)2 on carbon afforded a quantitative yield of (d,l)-1,2-diamino-1,2-dimethylcyclohexane, which was resolved to pure enantiomers with mandelic acid. This approach constitute a simple and potentially general route to interesting new chiral auxiliaries.

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