Type 1 Ring-Opening Reactions of Cyclopropanated 7-Oxabenzonorbornadienes with Organocuprates

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• 作者：Emily Carlson ; Jamie Haner ; Mary McKee ; William Tam
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：16
• 期：6
• 页码：1776-1779
• 全文大小：240K
• 年卷期：v.16,no.6(March 21, 2014)
• ISSN：1523-7052

文摘

For the first time, nucleophilic ring-openings of cyclopropanated 7-oxabenzonorbornadiene were investigated, providing a novel approach to the preparation of 2-methyl-1,2-dihydronaphthalen-1-ols. Satisfactory yields (up to 95%) were achieved using n-Bu₂CuCNLi₂ as the nucleophile and Et₂O as the solvent. The reaction demonstrated successful incorporation of primary, secondary, tertiary and aromatic nucleophiles, as well as ring-openings of substrates bearing arene substituents and C1-bridgehead substituents. A generalized mechanism for these transformations is also proposed.