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Use of a Semihollow‐Shaped Triethynylphosphane Ligand for Efficient Formation of Six‐ and Seven‐Membered Ring Ethers through Gold(I)‐Catalyzed Cyclization of Hydroxy‐Tethered Propargylic Esters
Author(s) -
Ito Hideto,
Harada Ayumi,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2013
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.201200949
Subject(s) - chemistry , cationic polymerization , piperidine , tetrahydropyran , ligand (biochemistry) , catalysis , ring (chemistry) , steric effects , derivative (finance) , sulfonamide , medicinal chemistry , bicyclic molecule , combinatorial chemistry , organic chemistry , biochemistry , receptor , financial economics , economics
The formation of six‐ and seven‐membered ring ethers from hydroxy‐tethered propargylic esters was efficiently catalyzed by a cationic gold(I) complex with a semihollow‐shaped triethynylphosphane ligand. This gold catalysis showed a tolerance toward the reactions of primary, secondary, and tertiary alcohol substrates with various substitution patterns. A sterically congested 2,2,6,6‐tetraalkyl‐substituted tetrahydropyran derivative as well as 6,6‐ and 7,6‐fused bicyclic diethers were obtained in useful yields. In addition, the gold catalysis was applicable to the reaction of a sulfonamide‐tethered propargylic ester to give a piperidine derivative.