Diastereoselective Synthesis of Spirocyclic Ether from ortho‐Carbonylarylacetylenols via Silver‐Catalyzed Cyclization under Acidic Conditions. Issue 15 (26th June 2021)

• Record Type: Journal Article
• Authors: Jaithum, Kanokwan; Tummatorn, Jumreang; Boekfa, Bundet; Thongsornkleeb, Charnsak; Chainok, Kittipong; Ruchirawat, Somsak
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 15(2021)
• Page Start: 3812
• Page End: 3834
• Publication Date: 2021-06-26
• Subjects: Silver -- Spiroether -- Stereoselective -- Ortho-Carbonylarylacetylenols -- Cyclization; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100548
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: ortho ‐Carbonylarylacetylenol, can be utilized for the synthesis of several important core structures. In this work, a method is developed for the diastereoselective synthesis of spirocyclic ethers using a silver catalyst under the presence of acid. This protocol can be applied to a variety of substrates resulting in the corresponding products in 35–97% yields with good diastereoselectivity. The proposed reaction mechanisms and stereoselectivity outcome of the corresponding products are investigated using DFT calculation. This current protocol can be applied to a broad range of substrates which would be useful for the creation of libraries of spirocylic ethers Abstract :