221110-45-8Relevant articles and documents
Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening
Fraile, José M.,García, Nuria,Herrerías, Clara I.,Mayoral, José A.
experimental part, p. 15 - 20 (2012/07/03)
The combination of two reactions in one-pot multistep system requires the compatibility not only between the catalysts of both reactions, but also between all the reaction components and conditions. In the case of the coupling of alkene epoxidation and epoxide ring opening, it has been possible to synthesize cyanohydrin and azidohydrin derivatives through a simple process that involves a one-pot multistep process by using a mixture of two heterogeneous catalysts, a silica-grafted Ti catalyst and ytterbium chloride, whose efficiency depends on the reactivity of the starting alkene. In addition, in some cases the mixture of catalysts can be recovered and reused in several one-pot multistep cycles. However, this system is not possible with electron-deficient alkenes, as the basic catalyst required for epoxidation has shown to be incompatible with the ring-opening process.
Reversibly addressing an allosteric catalyst in situ: Catalytic molecular tweezers
Gianneschi, Nathan C.,Cho, So-Hye,Nguyen, SonBinh T.,Mirkin, Chad A.
, p. 5503 - 5507 (2007/10/03)
Abiotic allosteric regulation: The design, synthesis, and application of novel, reversible allosteric catalytic molecular tweezers that contain a structural metal, addressable in situ, and two functional catalytic metals are reported (see picture). Kinetic and selectivity data reflect a significant decrease in cooperativity upon opening of the "arms" of the catalyst caused by reactions occurring at the hinge.
Metal(II) d-Tartarates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles
Yamashita, Hiroyuki
, p. 1213 - 1220 (2007/10/02)
The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartarates as heterogeneous chiral Lewis acid catalysts.The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartarate, and Zn(II) d-tartarate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42 percent ee, respectively.Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tatratate was studied.