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金催化(Z)-2-烯-4-炔-1-醇的环化反应:全取代二氢呋喃和呋喃的高效合成

Gold-catalyzed cyclization of (Z)-2-en-4-yn-1-ols: highly efficient synthesis of fully substituted dihydrofurans and furans.

作者信息

Liu Yuanhong, Song Feijie, Song Zhiquan, Liu Meina, Yan Bin

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China.

出版信息

Org Lett. 2005 Nov 24;7(24):5409-12. doi: 10.1021/ol052160r.

Abstract

[reaction: see text] The gold-catalyzed cyclization of (Z)-enynols offers an efficient and straightforward route to stereodefined (Z)-5-ylidene-2,5-dihydrofurans and fully substituted furans under extremely mild reaction conditions. Importantly, the results indicated that both the oxyauration and the proto-demetalation steps are highly stereoselective.

摘要

[反应:见正文] 在极其温和的反应条件下,(Z)-烯炔醇的金催化环化反应为立体专一的(Z)-5-亚基-2,5-二氢呋喃和全取代呋喃提供了一条高效且直接的合成路线。重要的是,结果表明氧金化和质子脱金属化步骤均具有高度的立体选择性。

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