Gold-Catalyzed Tandem C-C and C-O Bond Formation: A Highly Diastereoselective Formation of Cyclohex-4-ene-1,2-diol Derivatives

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• 作者：Choongmin Lim ; Ji-Eun Kang ; Ji-Eun Lee ; Seunghoon Shin
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：August 30, 2007
• 年：2007
• 卷：9
• 期：18
• 页码：3539 - 3542
• 全文大小：104K
• 年卷期：v.9,no.18(August 30, 2007)
• ISSN：1523-7052

文摘

We have reported an efficient gold(I)-catalyzed tandem cyclization of tert-butyl carbonate derivatives of hex-1-en-5-yn-3-ol where nucleophilicparticipation of the O-Boc group appears to intercept a carbocationic (or cyclopropyl carbene) Au intermediate. This novel protocol leads todensely functionalized cyclohexene-3,4-diol derivatives where 1,2- or 1,2,3-stereocenters are controlled in a highly diastereoselective fashion.