Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes.9. Synthesis and ring opening reactions of cis- and trans-oxides derived from 3-(benzyloxymethyl)cyclopentene and methyl 2-cyclopenten-1-carboxylate 1

Add time:09/10/2019    Source:sciencedirect.com

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 chelatc bidentate species in the opening process.

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