Catalytic [1, 3] O‐to‐C Rearrangement: Rapid Access to Bridged Bicyclic Systems. Issue 27 (19th April 2018)

• Record Type: Journal Article
• Authors: Zhang, Jiantao; Liao, Zhehui; Chen, Lianfen; Jiang, Huanfeng; Zhu, Shifa
• Is Part Of: Chemistry. Volume 24:Issue 27(2018)
• Page Start: 6927
• Page End: 6931
• Publication Date: 2018-04-19
• Subjects: [1, 3]-rearrangement -- [3, 3]-rearrangement -- bridged bicycles -- gold -- ring-expansion reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201801062
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A catalytic [1, 3] O‐to‐C rearrangement from enyne‐ethers was developed for the rapid synthesis of diverse bridged bicyclic systems. In this reaction, a vinyl oxonium intermediate, generated in situ from enyne‐ether, was the precursor for the [1, 3] O‐to‐C rearrangement. This versatile protocol represents the first example of catalytic [1, 3] O‐to‐C rearrangement based on ring‐expansion strategy, enabling efficient access to bridged bicyclic scaffolds. Abstract : The big OC : A catalytic [1, 3] O‐to‐C rearrangement from enyne‐ether was developed for the rapid synthesis of diverse bridged bicyclic systems. In this reaction, a vinyl oxonium intermediate, generated in situ from enyne‐ether, was the precursor for the [1, 3] O‐to‐C rearrangement. This versatile protocol represents the first example of catalytic [1, 3] O‐to‐C rearrangement based on ring‐expansion strategy, enabling efficient access to bridged bicyclic scaffolds.