Diastereoselective synthesis of cyclopentanoids with hydantoin and isoxazoline substituents

Article abstract of DOI:10.1021/jo9714831

Exploiting 1,3-dipolar cycloaddition and urea → hydantoin cyclization transformations, novel spiro-[cyclopenta[d]isoxazole-4'5-imidazolindine' heterocycles of generalized structure I have been prepared. The 1-amino-3- cyclopentenecarboxylate precursor II was prepared from a suitably activated/protected derivative of glycine and the bis-alkylating agent cis- 1,4-dichloro-2-butene.