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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

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Abstract:

Abstract

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.

Document Type: Communications

DOI: http://dx.doi.org/10.1002/adsc.201200949

Affiliations: Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan, phone: (+81)-11-706-3434, Fax: (+81)-11-706-3749

Publication date: March 11, 2013

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