Cu(OTf)₂-Catalyzed Selective Opening of Aryl and Vinyl Epoxides with Carbonyl Compounds to Give 1,3-Dioxolanes

Abstract

Copper(II) triflate catalyzes the ring-opening of aryl-and vinyl-substituted epoxides with various carbonyl compounds to furnish 1,3-dioxolanes under mild conditions. Alkyl-and alkoxycarbonyl-substituted epoxides remain unchanged under reaction conditions. This allows selective opening of aryl-substituted epoxides in the presence of alkyl-substituted ones.

Towards the Synthesis of the 4,19‐Diol Derivative of (–)‐Mycothiazole: Synthesis of a Potential Key Intermediate

“…To circumvent this problem, we tried to directly obtain the dioxolane adduct. Cu(OTf) 2 in acetone is known to selectively open vinylic epoxides, [34] but in our case only the starting material 29 was recovered. The use of BF 3 ·Et 2 O in acetone gave a mixture of degradation products.…”

Synthesis of Eight‐Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes

“…It is also worth noting that the substitution of an oxirane (e.g., 6 ) for the oxetane moiety does not carry a similar intermolecular reaction pattern with siloxy alkynes. Instead, when subjected to our standard reaction conditions, aldehyde 6 undergoes a known intermolecular homocyclization between the oxirane and the aldehyde functionalities,18 and no desired lactone product is observed. This observation can be explained by the higher reactivity (lower stability) of the oxirane relative to that of the oxetane functionality.…”

P46.08: Uterine arteriovenous malformation: Diagnosis through 3D power Doppler and angio resonance. A case report

“…It is also worth noting that the substitution of an oxirane (e.g., 6 ) for the oxetane moiety does not carry a similar intermolecular reaction pattern with siloxy alkynes. Instead, when subjected to our standard reaction conditions, aldehyde 6 undergoes a known intermolecular homocyclization between the oxirane and the aldehyde functionalities,18 and no desired lactone product is observed. This observation can be explained by the higher reactivity (lower stability) of the oxirane relative to that of the oxetane functionality.…”