Desymmetrization of meso 7-aza-2,3-bis(phenylsulfonyl) bicyclo[2.2.1]hept-2-ene: a re-examination. Kinetic resolution of racemic 3-arylsulfonyl-7-aza-2-bromobicyclo[2.2.1]hepta-2,5-dienes |
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| Authors: | Sergio Cossu Paola Peluso |
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| Institution: | a Dipartimento di Chimica, Università Ca’ Foscari di Venezia, Dorsoduro 2137, I-30123 Venezia, Italy
b Istituto di Chimica Biomolecolare ICB CNR, sezione di Sassari, Trav. La Crucca 3, Reg. Baldinca, I-07040 Li Punti, Sassari, Italy |
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| Abstract: | The inexpensive large scale preparation of N-methoxycarbonyl-7-aza-2,3-bis(phenylsulfonyl)bicyclo2.2.1]hept-2-ene and the re-examination of its stereoselective desymmetrization are reported. Moreover, the kinetic resolution of N-protected 3-arylsulfonyl-7-aza-2-bromobicyclo2.2.1]hepta-2,5-dienes promoted by (R,R)-hydrobenzoin is described, representing a new tool to fix the absolute stereochemistry of the 7-azabicyclo2.2.1] skeleton. |
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| Keywords: | Desymmetrization Kinetic resolution Epibatidine 7-Azabicyclo[2 2 1]heptane Sulfones |
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