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Paper | Regular issue | Vol 27, No. 12, 1988, pp.2839-2841
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4700
An Approach to the Enantioselective Synthesis of 2-Azabicyclo[2.2.1]hept-5-en-3-one

Olga Caamaño, Ana Eirín, Franco Fernández,* Generosa Gómez, and Eugenio Uriarte

*Departamento de Química Orgánica , Facultad de Farmacia, Universidad de Santiago de Compostela, E-15706, Santiago de Compostela, Spain

Abstract

2-Azabicyclo[2.2.1]hept-5-en-3-one (1) was obtained with a 13% enantiomeric excess by hydrolysis of the adduct formed by Diels-Alder addition of cyclopentadiene to the new chiral dienophile (+)-10-camphorsulphonyl cyanide (6) which was prepared in three steps from (+)-10-camphorsulphonic acid (3) in 44% overall yield.