Gold(I)/(III)-Catalyzed Synthesis of Cyclic Ethers; Valency-Controlled Cyclization Modes

被引：36

作者：

Morita, Nobuyoshi ^{[1
]}

Yasuda, Arisa ^{[1
]}

Shibata, Motohiro ^{[1
]}

Ban, Shintaro ^{[1
]}

Hashimoto, Yoshimitsu ^{[1
]}

Okamoto, Iwao ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Machida, Tokyo 1948543, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 11期

关键词：

MEYER-SCHUSTER REARRANGEMENT; HOMOGENEOUS GOLD CATALYSIS; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ALCOHOLS; BENZYLATION; KETONES; ACIDS; TETRAHYDROPYRANS; HETEROCYCLES; CARBOCYCLES;

D O I：

10.1021/acs.orglett.5b01046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Strategic use of oxophilic (hard) gold(III) and pi-philic (soft) gold(I) catalysts provides access to two types of cyclic ethers from propargylic alcohols. Thus, heating propargylic alcohols with an oxophilic gold(III) catalyst (AuBr3) results in cyclization to afford cyclic ethers bearing an acetylenic moiety, due to coordination of gold(III) to the oxygen of the propargylic hydroxyl group. On the other hand, propargylic alcohols with a pi-philic gold(I) catalyst (Ph3PAuNTf2) induces MeyerSchuster rearrangement to afford alpha,beta-unsaturated ketones, which undergo gold(III)-catalyzed intramolecular oxa-Michael addition to afford cyclic ethers bearing a carbonyl group, due to coordination of gold(III) to the oxygen of the carbonyl group.

引用

页码：2668 / 2671

页数：4

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