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Asymmetric Synthesis of 3,4-Diaminocyclohexanol and endo-7-Azabicyclo[2.2.1]heptan-2-amine

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journal contribution
posted on 05.11.2010, 00:00 by Diego Savoia, Stefano Grilli, Andrea Gualandi
Hydroboration of (1R,2R)-bis[(S)-1-phenylethylamino]cyclohex-4-ene and its derivatives with several borane reagents gave diastereomeric mixtures of the 3,4-diaminocyclohexanol derivatives. Cyclization of the prevalent diastereomer with the R configuration of the newly formed stereocenter under Mitsunobu conditions, followed by reductive removal of the N-substituents, gave the optically pure endo-7-azabicyclo[2.2.1]heptane-2-amine.