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Paper | Regular issue | Vol 45, No. 9, 1997, pp.1745-1750
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7872
Inversion of Enantioselectivity in the Diels-Alder Synthesis of 2-Azabicyclo- [2.2.1]hept-5-en-3-one from Cyclopentadiene and Chiral Sulfonyl Cyanides

José M. Blanco, Olga Caamaño, Franco Fernández,* Xerardo García-Mera, Isabel Nieto, and José E. Rodríguez-Borges

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

Abstract

Diels-Alder cycloaddition of (1R,3S,4S)-3-methanesulfonyl cyanide to cyclopentadiene, followed by treatment with AcOH/H2O, afforded an 11% ee of (+)-(1S)-2-azabicyclo[2.2.1]hept-5-en-3-one [(+)-ent-1]. The analogous process from (1R,3R,4S)-3-methanesulfonyl cyanide afforded an estimated 12% ee of (-)-1.