Lewis Acid Catalyzed Carbon鈭扖arbon Bond Cleavage of Aryl Oxiranyl Diketones: Synthesis of cis-2,5-Disubstituted 1,3-Dioxolanes

详细信息    查看全文

• 作者：Zuliang Chen ; Lai Wei ; Junliang Zhang
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：March 4, 2011
• 年：2011
• 卷：13
• 期：5
• 页码：1170-1173
• 全文大小：745K
• 年卷期：v.13,no.5(March 4, 2011)
• ISSN：1523-7052

文摘

Carbonyl ylide is one of the most important intermediates which can undergo a series of 1,3-dipolar cycloaddition reactions. The C鈭扖 heterolysis of oxirane is believed to be the most atom-economic and straightforward way to generate carbonyl ylide. However, this chemistry was only achieved under photochemical and thermal conditions in past years. In this work, the one-step diastereoselective synthesis of cis-2,5-disubstituted 1,3-dioxolanes via [3 + 2] cycloadditions of aldehydes and carbonyl ylide, which is obtained from Lewis acid catalyzed C鈭扖 bond heterolysis of aryl oxiranyl diketones at ambient temperature, is described.