An Efficient Synthesis of Benzazocines by Gold(I)‐Catalyzed Tandem 1, 2‐Acyloxy Shift/[3+2] Cycloaddition of Terminal 1, 9‐Enynyl Esters. Issue 15 (19th July 2016)

• Record Type: Journal Article
• Authors: Feng, Shangbiao; Wang, Zhengshen; Zhang, Weiwei; Xie, Xingang; She, Xuegong
• Is Part Of: Chemistry, an Asian journal. Volume 11:Issue 15(2016)
• Page Start: 2167
• Page End: 2172
• Publication Date: 2016-07-19
• Subjects: cycloaddition -- fused-ring systems -- gold -- homogeneous catalysis -- nitrogen heterocycles; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201600593
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: An effective synthesis of structurally diverse benzazocines was accomplished in good to excellent chemical yields (55–82 %) through a gold(I)‐catalyzed cascade reaction involving tandem 1, 2‐acyloxy shift/[3+2] cycloaddition of terminal 1, 9‐enynyl esters. The reaction proceeds under extremely mild conditions and represents one of the relatively few transition‐metal‐catalyzed intramolecular cycloaddition reactions for the synthesis of benzazocines. Abstract : Public N‐emy : The synthesis of structurally diverse benzazocines is accomplished in yields of 55–82 % through a gold(I)‐catalyzed cascade reaction involving the tandem 1, 2‐acyloxy shift/[3+2] cycloaddition of terminal 1, 9‐enynyl esters. The reaction proceeds under extremely mild conditions and represents one of the relatively few transition‐metal‐catalyzed intramolecular cycloaddition reactions for benzazocine synthesis. Ts=4‐MeC6 H4 SO2 .