Alkyl- and arylation of oxacyclic ethers with triethylsilyl triflate-2,4,6-collidine-Gilman reagent combination: Remarkable discrimination of two ether oxygens

被引：9

作者：

Fujioka, Hiromichi ^{[1
]}

Ohnaka, Takuya ^{[1
]}

Okitsu, Takashi ^{[1
]}

Kubo, Ozora ^{[1
]}

Okamoto, Kazuhisa ^{[1
]}

Sawama, Yoshinari ^{[1
]}

Kita, Yasuyuki ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

HETEROCYCLES | 2007年 / 72卷

关键词：

D O I：

10.3987/COM-06-S(K)46

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：529 / 540

页数：12

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