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Diastereoselective Synthesis of Spirocyclic Ether from ortho ‐Carbonylarylacetylenols via Silver‐Catalyzed Cyclization under Acidic Conditions
Author(s) -
Jaithum Kanokwan,
Tummatorn Jumreang,
Boekfa Bundet,
Thongsornkleeb Charnsak,
Chainok Kittipong,
Ruchirawat Somsak
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100548
Subject(s) - chemistry , stereoselectivity , catalysis , ether , combinatorial chemistry , organic chemistry
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