Development of a Highly Efficient Catalytic Method for Synthesis of Vinyl Ethers

Abstract

A new method for the preparation of alkyl vinyl ethers has been developed. Thus, various types of alkyl vinyl ethers were synthesized by the reaction of alcohols with vinyl acetate under the influence of a catalytic amount of [Ir(cod)Cl]2 combined with Na2CO3 in good to excellent yields.

A Unified Strategy Targeting the Thiodiketopiperazine Mycotoxins Exserohilone, Gliotoxin, the Epicoccins, the Epicorazines, Rostratin A and Aranotin

“…After extensive screening for selective deprotection of the primary alcohol function, we identified HF/pyridine as the reagent of choice, [40] giving the monoprotected bisalcohol 36 in excellent yield. The hydroxy function was vinylated in the presence of an iridium catalyst, as reported by Okimoto et al [41] Treatment of 36 with vinyl acetate in the presence of [IrA C H T U N G T R E N N U N G (cod)Cl] 2 (cod = 1,5-cyclooctadiene) as the catalyst provided the enol ether 38. We then attempted the enol etherolefin RCM for the preparation of the oxepine ring in 40.…”

Macromolecular Recognition of Cyclodextrin: Inversion of Selectivity of β‐Cyclodextrin toward Adamantyl Groups Induced by Macromolecular Chains

“…1-Adamantyl vinyl ether (AdVE) was supplied from Maruzen Petrochemical (Tokyo, Japan) and used as received. 4-(1-Adamantyl)phenyl vinyl ether (AdPhVE) was prepared according to the procedure reported by Okimoto et al [8] Sodium 1-adamantanecarboxylate (AdA) and sodium 4-(1-adamantyl)benzoate (AdPhA) were prepared from neutralization of 1-adamantanecarboxylic acid and 4-(1-adamantyl)phenylcarboxylic acid [9] with aqueous sodium hydroxide. Diethyl ether (Et 2 O), tetrahydrofuran (THF), and toluene were purified by utilizing a GlassContour solvent dispending system.…”

Synthesis of 3-Substituted-clavams: Antifungal Properties, DD-Peptidase and β-Lactamase Inhibition

“…The simple vinyl ether 23 was obtained directly from 16 (Scheme 2) using the standard trans-etherification procedure with vinyl n-butyl ether in the presence of mercury acetate [22], or by the alternative method, involving reaction of the alcohol with vinyl acetate in the presence of [IrCl(cod)] 2 [23]. It should be stressed that both TIBS-protected vinyl and (Z)-propenyl ethers derived from the phenyl-1,2-ethanediol displayed the same direction and a similar relatively high degree of asymmetric induction [18].…”