The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the oxirane systems derived from cyclopentene bearing a polar functionality (CH2OBn or COOMe) in a homoallylic relationship to the oxirane ring. The cis/trans diastereoisomeric epoxide pairs 7-8 and 9-10 derived from 3- (benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate, respectively, were prepared and some of their opening reactions were studied. The regioselectivity observed turned out to depend on the opening reaction protocol (standard or metal-assisted), suggesting the efficacious incursion, under the appropriate conditions, of chelate bidentate species in the opening process.

REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .9. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 3-(BENZYLOXYMETHYL)CYCLOPENTENE AND METHYL 2-CYCLOPENTEN-1-CARBOXYLATE

CROTTI, PAOLO;DI BUSSOLO, VALERIA;FAVERO, LUCILLA;PINESCHI, MAURO
1995-01-01

Abstract

The regiochemical outcome of the ring opening of 1,2-epoxides through chelation processes assisted by metal ions, was verified in the oxirane systems derived from cyclopentene bearing a polar functionality (CH2OBn or COOMe) in a homoallylic relationship to the oxirane ring. The cis/trans diastereoisomeric epoxide pairs 7-8 and 9-10 derived from 3- (benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate, respectively, were prepared and some of their opening reactions were studied. The regioselectivity observed turned out to depend on the opening reaction protocol (standard or metal-assisted), suggesting the efficacious incursion, under the appropriate conditions, of chelate bidentate species in the opening process.
1995
Colombini, M; Crotti, Paolo; DI BUSSOLO, Valeria; Favero, Lucilla; GARDELLI C, MACCHIA F; Pineschi, Mauro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/174616
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