Mutual Cooperation in the Formal Allyl Alcohol Nucleophilic Substitution and Hydration of Alkynes for the Construction of γ‐Substituted Ketones. Issue 19 (22nd March 2016)

• Record Type: Journal Article
• Authors: Huang, Kaimeng; Wang, Hongkai; Liu, Lingyan; Chang, Weixing; Li, Jing
• Is Part Of: Chemistry. Volume 22:Issue 19(2016)
• Page Start: 6458
• Page End: 6465
• Publication Date: 2016-03-22
• Subjects: 1, 5-enynols -- cyclization -- gold catalysis -- hydration -- nucleophilic substitution -- ring-opening reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600248
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ‐functionalized ketones with high to excellent yields. This reaction actually involved an intramolecular O−H insertion cyclization of an alkyne to form the dihydrofuran intermediate, which was followed by the nucleophilic addition ring‐opening of a dihydrofuran to give the target compound. Abstract : Cooperation is key ! Mutual cooperation in the formal allyl alcohol nucleophilic substitution reaction and hydration of an alkyne has been utilized in the presence of a gold catalyst to give a series of γ‐functionalized ketones with high to excellent yields (see scheme).