General, Stereoselective Synthesis of (Z)-β,γ-Unsaturated Nitriles Promoted by Samarium Diiodide

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• 作者：José ; M. Concelló ; n ; Humberto Rodrí ; guez-Solla ; Carmen Simal ; David Santos ; Nieves R. Paz
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：October 16, 2008
• 年：2008
• 卷：10
• 期：20
• 页码：4549-4552
• 全文大小：110K
• 年卷期：v.10,no.20(October 16, 2008)
• ISSN：1523-7052

文摘

A method to obtain (Z)-β,γ-unsaturated nitriles in high or good yields and with moderate or high stereoselectivity is described. The products were achieved through the photoinduced metalation of 3-acetoxy-4-chloronitriles with SmI₂. The starting compounds were readily prepared, and a mechanism is proposed to explain this stereoselective β-elimination reaction.