Alkyl- and Arylation of Oxacyclic Ethers with Triethylsilyl Triflate—2,4,6-Collidine—Gilman Reagent Combination: Remarkable Discrimination of Two Ether Oxygens
摘要:
The alkylation reaction of oxacyclic ethers such as THP-ethers, THF-ethers, etc., has been developed. The treatment of oxacyclic ether with TESOTf and 2,4,6-collidine gives the collidinium salt intermediate obtained by the reaction of the cyclic oxygen atom. The addition of Gilman reagent to the mixture gives the alkylated product. The reaction proceeds with high chemoselectivity though there are two different oxygen atoms in the oxacyclic ethers.