51209-80-4

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 286-20-4 cyclohexane-1,2-epoxide 
• 7677-24-9 trimethylsilyl cyanide 
• 286-20-4 cyclohexene oxide 
• 2754-27-0 trimethylsilyl acetate 
• 110-83-8 cyclohexene 
• 4648-54-8 trimethylsilylazide 
• 63591-12-8 trimethylsilyl 2-methoxyacetate 
• 64230-01-9 2-formyl-2-chlorocyclohexanone 
• 18027-10-6 sodium trimethylsilanolate 
• 1561-86-0 2-chlorocyclohexanol 

Downstream Products

• 1561-86-0 2-chlorocyclohexanol 
• 6628-80-4 trans-2-chlorocyclohexanol 

Relevant academic research and scientific papers

Enantiotopic Discrimination by Coordination-Desymmetrized meso-Ligands

The first examples of enantiopure catalysts that are chiral merely due to coordination of different metal ions at enantiotopic positions of an achiral meso-ligand are reported. These catalysts exhibit a pseudo-Cs symmetry and are able to catalyze reactions demanding simultaneous involvement of two catalytic sites. The latter was demonstrated by application in the asymmetric ring-opening of meso-epoxides.

Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening

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.

1,2-Ferrocenediylazaphosphinines 2: A new class of nucleophilic catalysts for ring-opening of epoxides

1,2-Ferrocenediylazaphosphinines (1a-c) have been successfully employed as a new class of nucleophilic catalysts for ring-opening of a range of epoxides, their catalytic efficiency in terms of regioselectivity as well as chemical yield comparing well with the existing catalysts in the literature. In contrast, low enantiomeric excesses have been obtained from the reactions of meso-epoxides catalyzed by (R)-1.

Dichlorotin oxide-catalyzed new direct functionalization of olefins: Synthesis of trans β-azidohydrins and 1,2-diols

We have succeeded in developing direct syntheses of trans β- azidohydrins and trans 1,2-diol derivatives from olefins catalyzed by dichlorotin oxide. The regioselectivity of these reactions with tri- substituted olefins is high (10:1 in the synthesis of 1,2-diol derivatives) to excellent (>99:1 in the synthesis of azidohydrins). It has been found that these reactions do not proceed via epoxides. (C) 2000 Elsevier Science Ltd.

Facile O-silylation of tertiary alcohols in the presence of Mg-metal

Treatment of aliphatic alcohols with trimethylsilyl chloride (TMSCl) in N,N-dimethylformamide (DMF) containing Mg-turning at room temperature brought about facile and efficient O-silylation to give the corresponding trimethylsilyl ethers in good to excellent yields. This method can be also available for sterically hindered tert-alcohols and alcohols having a variety of substituents which may be labile under the basic conditions used in the conventional O-silylation.

Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.

The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic depen

SODIUM BROMIDE CATALYSED REGIOSELECTIVE CLEAVAGE OF OXIRANES WITH CHLOROTRIMETHYLSILANE

Sodium bromide efficiently catalyses the regioselective cleavage of oxiranes with chlorotrimethylsilane to the corresponding O-silyiated chlorohydrins in excellent yield.

Cobalt(II) Chloride Catalysed Regioselective Cleavage of Oxiranes with Chlorotrimethylsilane

Oxiranes can be cleaved regioselectively with chlorotrimethylsilane in presence of cobalt(II) chloride to the corresponding O-silylated vicinal chlorohydrins in excellent yields.