32426-79-2Relevant articles and documents
Novel Synthesis of Enol Ethers from β-Alkoxy Alcohols through t-BuOK-Promoted Elimination Reaction
Otera, Junzo,Niibo, Yoshihisa
, p. 3977 - 3978 (1986)
A new synthesis of enol ethers from β-alkoxy alcohols was achieved through a t-BuOK-promoted elimination reaction.
Ruthenium(IV)-catalyzed isomerization of the C=C bond of O-allylic substrates: A theoretical and experimental study
Varela-Ulvarez, Adrian,Sordo, Jose A.,Piedra, Estefania,Nebra, Noel,Cadierno, Victorio,Gimeno, Jose
experimental part, p. 10583 - 10599 (2011/11/06)
A general mechanism to rationalize RuIV-catalyzed isomerization of the C=C bond in O-allylic substrates is proposed. Calculations supporting the proposed mechanism were performed at the MPWB1K/6-311+G(d,p)+SDD level of theory. All experimental observations in different solvents (water and THF) and under different pH conditions (neutral and basic) can be interpreted in terms of the new mechanism. Theoretical analysis of the transformation from precatalyst to catalyst led to structural identification of the active species in different media. The experimentally observed induction period is related to the magnitudes of the energy barriers computed for that process. The theoretical energy profile for the catalytic cycle requires application of relatively high temperatures, as is experimentally observed. Participation of a water molecule in the reaction coordinate is mechanistically essential when the reaction is carried out in aqueous medium.
Synthesis of tert-alkyl amino hydroxy carboxylic esters via an intermodular ene-type reaction of oxazolones and enol ethers
Mosey, Robert A.,Fisk, Jason S.,Friebe, Timothy L.,Tepe, Jetze J.
supporting information; experimental part, p. 825 - 828 (2009/04/07)
terf-Alkyl amino hydroxy carboxylic acids are abundantly present within the structure of many biologically active natural products. We describe herein the synthesis of these substrates using an oxazolone-mediated ene-type reaction with enol ethers followed by NaBH4 reduction of the intermediate oxazolone.
Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles
Arisawa, Mitsuhiro,Terada, Yukiyoshi,Takahashi, Kazuyuki,Nakagawa, Masako,Nishida, Atsushi
, p. 4255 - 4261 (2007/10/03)
A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.
