36713-55-0Relevant academic research and scientific papers
Influence of Alcohol β-Fluorination on Hydrogen-Bond Acidity of Conformationally Flexible Substrates
Graton, Jerome,Compain, Guillaume,Besseau, Francois,Bogdan, Elena,Watts, Joseph M.,Mtashobya, Lewis,Wang, Zhong,Weymouth-Wilson, Alex,Galland, Nicolas,Le Questel, Jean-Yves,Linclau, Bruno
, p. 2811 - 2819 (2017/03/05)
Rational modulations of molecular interactions are of significant importance in compound properties optimization. We have previously shown that fluorination of conformationally rigid cyclohexanols leads to attenuation of their hydrogen-bond (H-bond) donat
Hybrid Organo- and Biocatalytic Process for the Asymmetric Transformation of Alcohols into Amines in Aqueous Medium
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,Rebolledo, Francisca,González-Sabín, Javier
, p. 4768 - 4774 (2017/07/24)
A hybrid organo- and biocatalytic system for the asymmetric conversion of racemic alcohols into amines was developed. Combining an organocatalyst, AZADO, an oxidant, NaOCl, and an enzyme, ω-transaminase, we implemented a one-pot oxidation-transamination sequential process in aqueous medium. The method showed broad substrate scope and was successfully applied to conventional secondary alcohols and sterically hindered β-substituted cycloalkanols, where a highly stereoselective dynamic asymmetric bioamination enabled us to set up both contiguous stereocenters with very high enantio- and diastereomeric ratio (>90% yield, >99% ee, and up to 49:1 dr).
Acid-catalyzed reaction of 2-hydroxycyclobutanone with benzylic alcohols
Martis, Alberto,Luridiana, Alberto,Frongia, Angelo,Arca, Massimiliano,Sarais, Giorgia,Aitken, David J.,Guillot, Regis,Secci, Francesco
, p. 10053 - 10063 (2017/12/26)
The acid-promoted syntheses of 2-(benzyloxy)cyclobutanones and bis(benzyloxy)dioxatricyclo decanes were achieved starting from 2-hydroxycyclobutanone and variously functionalized benzyl alcohols. The reaction sequences afforded the desired products in good to high yields and in a solvent-dependent chemoselective fashion.
An efficient synthesis of 3-alkyl-1,5,3-dioxazepanes and their use as electrophiles in double-Mannich reactions
Sparrow, Kevin,Barker, David,Brimble, Margaret A.
, p. 1017 - 1028 (2012/02/13)
An efficient synthesis of 3-alkyl 1,5,3-dioxazepanes was developed for subsequent use in double-Mannich reactions with a variety of carbon-based nucleophiles. It was found that addition of methyltrichlorosilane to the dioxazepane led to a long-lasting rea
Asymmetric synthesis of O-protected acyloins using enoate reductases: Stereochemical control through protecting group modification
Winkler, Christoph K.,Stueckler, Clemens,Mueller, Nicole J.,Pressnitz, Desiree,Faber, Kurt
supporting information; experimental part, p. 6354 - 6358 (2011/02/24)
O-Protected cyclic acyloins were obtained in nonracemic form through asymmetric bioreduction of α,β-unsaturated alkoxy ketones by using 11 different enoate reductases from the "Old Yellow Enzyme" family. The stereochemical outcome of the biotransformation could be switched by variation of the O-protecting group or by the ring size of the substrate, which allows access to both stereoisomers in up to >97 % ee Whereas α-alkoxy enones were readily accepted as substrates, β-analogs were not converted. Overall, α-alkoxy enones represent a novel type of substrate for flavin-dependent ene-reductases. Copyright
Simple and efficient MW-assisted cleavage of acetals and ketals in pure water
Procopio, Antonio,Gaspari, Marco,Nardi, Monica,Oliverio, Manuela,Tagarelli, Antonio,Sindona, Giovanni
, p. 8623 - 8627 (2008/03/30)
Simple and efficient MW-assisted cleavage of acetal and ketal is proposed in deionized water and in a very short time.
Er(OTf)3 as a mild cleaving agents for acetals and ketals
Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Nardi, Monica,Procopio, Antonio,Tagarelli, Antonio
, p. 496 - 498 (2007/10/03)
Er(OTf)3 is proposed as a very gentle Lewis acid catalyst in a chemoselective method for the cleavage of alkyl and cyclic acetals and ketals at room temperature in wet nitromethane is presented.
Multicatalytic processes using diverse transition metals for the synthesis of alkenes
Lebel, Helene,Paquet, Valrie
, p. 11152 - 11153 (2007/10/03)
A series of cascade processes for the synthesis of alkenes from alcohols is described. Each individual step is catalyzed with a specific transition metal complex. The oxidation-methylenation one-pot procedure took place in the presence of a palladium and a rhodium catalyst to produce the desired terminal alkenes in high yields. A methylenation-ring-closing metathesis allowed the synthesis of cyclic alkenes from carbonyl derivatives, using the second-generation metathesis catalyst. Finally, an oxidation-methylenation-RCM process that involves up to three different transition metal catalysts in the same vessel is presented. Copyright
Simple and efficient chemoselective mild deprotection of acetals and ketals using cerium(III) triflate
Dalpozzo, Renato,De Nino, Antonio,Maiuolo, Loredana,Procopio, Antonio,Tagarelli, Antonio,Sindona, Giovanni,Bartoli, Giuseppe
, p. 9093 - 9095 (2007/10/03)
A new and chemoselective method for the cleavage of alkyl and cyclic acetals and ketals at room temperature in wet nitromethane by using catalytic cerium(III) trifluoromethane sulfonate is presented. The high yields, the observed selectivity, the very gentle reaction conditions, and the almost neutral pH make this procedure particularly attractive for multistep synthesis.
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Pineschi, Mauro,Marianucci, Francesco,Renzi, Gabriele,Amici, Giuseppina,Roselli, Graziella
, p. 7513 - 7524 (2007/10/03)
The regiochemical behavior of cyclohexene oxides bearing a remote O-functionality was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D3/+, C(n)H5/+, Me2F+
