98088-48-3Relevant academic research and scientific papers
Silylcyclopropanes by Selective [1,4]-Wittig Rearrangement of 4-Silyl-5,6-dihydropyrans
Mori-Quiroz, Luis M.,Maloba, Emmanuel W.,Maleczka, Robert E.
supporting information, p. 5724 - 5728 (2021/07/31)
4-Silyl-5,6-dihydropyrans undergo remarkably selective [1,4]-Wittig rearrangements to give silylcyclopropanes in good yields. The selectivity is independent of the silyl group, but it is influenced by the electronic character of the migrating center. Elec
A Scalable Membrane Pervaporation Approach for Continuous Flow Olefin Metathesis
Breen, Christopher P.,Parrish, Christine,Shangguan, Ning,Majumdar, Sudip,Murnen, Hannah,Jamison, Timothy F.,Bio, Matthew M.
supporting information, p. 2298 - 2303 (2020/05/14)
The translation of olefin metathesis reactions from the laboratory to process scale has been challenging with traditional batch techniques. In this contribution, we describe a continuous membrane reactor design that selectively permeates the ethylene byproduct from metathetical processes, thereby overcoming the mass-transport limitations that have negatively influenced the efficiency of this transformation in batch vessels. The membrane sheet-in-frame pervaporation module yielded turnover numbers of >7500 in the case of diethyl diallylmalonate ring-closing metathesis. The preparation of more challenging, low-effective-molarity substrates, a cyclooctene and a 14-membered macrocyclic lactone, was also effective. A comparison of optimal membrane reactor conditions to a sealed tubular reactor revealed that the benefits of ethylene removal are most apparent at low reaction concentrations.
Bronsted acid-catalyzed three-component hosomi-sakurai reactions
Kampen, Daniela,Ladepeche, Arnaud,Classen, Gerrit,Lista, Benjamin
experimental part, p. 962 - 966 (2009/05/27)
Aldehydes react with silyl ethers or the corresponding alcohols and allylsilanes in the presence of catalytic amounts of 2,4-dinitrobenzenesulfonic acid (DNBA) to provide a wide range of homoallylic ethers in moderate to high yields.
Iron(III) p-toluenesulfonate catalyzed synthesis of homoallyl ethers from acetals and aldehydes
Spafford, Matthew J.,Anderson, Erin D.,Lacey, Joshua R.,Palma, Ann C.,Mohan, Ram S.
, p. 8665 - 8667 (2008/03/30)
Iron(III) p-toluenesulfonate, Fe(OTs)3·6H2O, is an inexpensive, versatile and commercially available catalyst for the allylation of acetals using allyltrimethylsilane to yield homoallyl ethers in moderate to good yields. The one-pot
Trimethylsilyl trifluoromethanesulfonate catalyzed one-pot method for the conversion of aldehydes to homoallyl ethers in an ionic liquid
Anzalone, Peter W.,Mohan, Ram S.
, p. 2661 - 2663 (2007/10/03)
A mild method for the trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed one-pot synthesis of homoallyl ethers from aldehydes has been developed in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([bmim] [OTf]). The advanta
Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate
Anzalone, Peter W.,Baru, Ashvin R.,Danielson, Eric M.,Hayes, Patrick D.,Nguyen, Mai P.,Panico, Ambrose F.,Smith, Russell C.,Mohan, Ram S.
, p. 2091 - 2096 (2007/10/03)
(Chemical Equation Presented) Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)3? xH 2O (1 x 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by
Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence
Schmidt, Bernd
, p. 7672 - 7687 (2007/10/03)
A novel ruthenium-catalyzed tandem ring-closing metathesis (RCM) double-bond isomerization reaction is described in this paper. The utility of this method for the efficient syntheses of five-, six-, and seven-membered cyclic enol ethers is demonstrated. It relies on the conversion of a metathesis-active ruthenium carbene species to an isomerization-active ruthenium-hydride species in situ. This conversion is achieved by using various additives. Scope and limitations of the different protocols are discussed, and some mechanistic considerations based on 31P and 1H NMR spectroscopic studies are presented.
Synthesis of conjugated γ- and δ-lactones from aldehydes and ketones via a vinylation(allylation)-ring closing metathesis-oxidation sequence
Marco, J. Alberto,Carda, Miguel,Rodríguez, Santiago,Castillo, Encarnación,Kneeteman, María N.
, p. 4085 - 4101 (2007/10/03)
Nucleophilic C-vinylation and C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl or homoallyl ethers, respectively. Ring-closing metathesis of these compounds afforded in many cases cyclic ethers (dihydrofurans and dihydropyrans, respectively) bearing disubstituted and trisubstituted C=C bonds. These were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones. Reasons for the observed failures are presented and discussed.
Catalytic allylation of aldehydes with allyltrimethylsilane using in situ-generated trimethylsilyl methanesulfonate (TMSOMs) as a catalyst
Wang, Ming Wen,Chen, Yong Jun,Wang, Dong
, p. 385 - 387 (2007/10/03)
One-pot allylation reactions of carbonyl compounds with allyltrimethylsilane catalyzed by in situ-generated TMSOMs were carried out. TMSOMs was found to be an efficient catalyst in the allylation of the hydrates of α-keto aldehyde and glyoxylate. In situ-generated TMSOMs also can catalyze the SMS reaction of the aldehydes giving the functionalized homoallylic ethers in good to excellent yields.
Epoxide opening reactions of aryl substituted dihydropyran oxides: Regio- And stereochemical studies directed towards deoxy-aryl-Cglycosides
Schmidt, Bernd
, p. 2627 - 2637 (2007/10/03)
2-Aryl-substituted tetrahydropyrans with 3,4- or 4,5-/ra;w-configured oxo substituents have been synthesized via ring-closing metathesis of allyl homoallyl ethers, epoxidation of the resulting dihydropyrans and opening of the epoxides with O-nucleophiles
