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Short Paper | Regular issue | Vol 96, No. 1, 2018, pp.152-157
Published online, 14th December, 2017
DOI: 10.3987/COM-17-13834
Diastereospecific Intramolecular Cyclopropanation of Enantiopure 8-Bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-ones

Anna Vargas, María L. Orea,* Dino Gnecco,* David M. Aparicio, Jorge R. Juárez, and Joel L. Terán

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC9, Complejo de Ciencias, C.U. 72570 Puebla, Pue., Mexico


A diastereospecific intramolecular cyclopropanation of (3R,8R,8aS)-8-bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one 1 and (3R,8S,8aS)-8-bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-one 2 to generate the corresponding enantiopure 3-phenylhexahydro-5H-cyclopropa[3,4]pyrrolo[2,1-b]oxazol-5-ones 3 and 4 in high yield is described.