81601-68-5

Upstream product

• 875-03-6 3,3-dimethyl-spiro[norbornan-2,2'-oxirane] 
• 79-92-5 camphene 
• 542-92-7 cyclopenta-1,3-diene 
• 374895-87-1 C₁₀H₁₄O 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 875-03-6 (+/-)-camphene oxide 
• 565-00-4 dl-camphene 
• 5056-10-0 acetic acid-(3,3-dimethyl-[2]norbornylidenemethyl ester) 
• 15780-34-4 1-(3,3-Dimethyl-bicyclo<2.2.1>hept-2-yl)ethanon 
• 15780-45-7 (+/-)-1-(3,3-dimethyl-norborn-5-ene-2-endo-yl)-ethanone 
• 20440-73-7 (+/-)-2,2-dimethyl-3-((Ξ)-nitromethylene)-norbornane of mp: 65 degree 
• 67519-00-0 2-exo-10-camphanoic acid 
• 85506-67-8 endo-2,2-dimethylbicyclo<2.2.1>heptane-3-carboxylic acid 

Downstream Products

• 155323-17-4 (5S)-4-aza-2-oxa-6,6-dimethyl-7,10-methylene-5-spiro<4.5>decan-3-one 
• 155227-25-1 C₂₀H₂₃NO₃ 
• 155227-27-3 C₂₅H₂₉NO₃ 
• 81572-05-6 <α-2H2>benzyl camphyl thioether 
• 81601-69-6 tosylate of endo-camphanol 
• 94200-95-0 1-(3,3-Dimethyl-bicyclo<2.2.1>hept-2-yl)-2-methyl-propan-2-ol 
• 2226-08-6 2-(3,3-Dimethyl-bicyclo<2.2.1>hept-2-yl)-ethanol 

Relevant academic research and scientific papers

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Acceleration of Enantioselective Cycloadditions Catalyzed by Second-Generation Chiral Oxazaborolidinium Triflimidates by Biscoordinating Lewis Acids

The activation of second-generation fluorinated oxazaborolidines by the strong acid triflimide (Tf2NH) in CH2Cl2 solution leads to highly active chiral Lewis acids that are very effective catalysts for (4 + 2) cycloaddition. We report herein that this catalytic activity can be further enhanced by the use of Tf2NH in combination with the biscoordinating Lewis acid TiCl4 or SnCl4 as a coactivator. The effective increase in acidity of an exceedingly strong protic acid is greater for biscoordinating TiCl4 and SnCl4 than for monocoordinating salts, even the strong Lewis acids AlBr3 and BBr3 in CH2Cl2 or CH2Cl2/toluene. The increase in the effective acidity of Tf2NH can be understood in terms of a stabilized cyclic anionic complex of Tf2N- and TiCl4, which implies a broader utility than that described here. The utility of Tf2NH-TiCl4 activation of fluorinated oxazaborolidines is documented by examples including the first enantioselective (4 + 2) cycloaddition to α,β-unsaturated acid chlorides.

Preparation of polyfunctional phosphines using zinc organometallics

The reaction of functionalized diorganozincs with chlorodiorganophosphines provides polyfunctional phosphines in good yields. Especially attractive is the hydroboration/boron-zinc exchange sequence which allows the conversion of functionalized olefins into polyfunctional phosphines in a one-pot procedure. Several new chiral phosphines have been prepared starting from readily available chiral olefins (terpenes) and their efficiency in asymmetric hydrogenation reactions has been evaluated.

Novel Reduction of Carboxylic Acids and Hydroboration of Olefins by Electrolysis of Sodium Borohydride

Electrochemical oxidation of sodium borohydride in diglyme containing aliphatic or aromatic carboxylic acids followed by acid-catalyzed hydrolysis afforded the corresponding primary alcohols in good yields.Furthermore, similar electrochemical oxidation in the presence of a variety of olefins instead of carboxylic acids, followed by treatment with alkaline-hydrogen peroxide, brought about novel electrochemical hydroboration to give the corresponding alcohols regio- and stereoselectively in good yields.

A Facile Conversion of Alkenes to Alcohols with Benzyltriethylammonium Borohydride-Chlorotrimethylsilane

A combination of benzyltrimethylammonium borohydride and chlorotrimethylsilane (1:1) in dichloromethane at 0 deg C has been found to be a convenient reagent system for the conversion of alkenes to alcohols, the hydroxy group of which is introduced in an anti-Markovnikov manner.

Oxygenation of Oleefinic Hydrocarbons Catalyzed by Iron(II) Acetonitrile Solvate

Oxygenation reactions of olefins having an endo- or exo-cyclic double bond, namely, cyclohexene, norbornene, camphene, longifolene, and ent-kaurene, with a simple model reagent, Fe(MeCN)62+-H2O2-Ac2O, for mono-oxygenase were investigated in connection with their biotransformations.Keywords oxygenation; olefin; endo-cyclic double bond; exo-cyclic double bond; iron(II) acetonitrile solvate; hydrogen peroxide; model enzyme; mono-oxygenase

Novel Method for Hydroboration of Olefins Using Electrolysis

A first example of electrochemical hydroboration of olefins was found.Anodic oxidation of sodium borohydride in the presence of olefins in diglyme followed by conventional oxidation gave the corresponding alcohols regio- and stereoselectively in good yields.

A Convenient One-pot Hydroboration / Isomerization / Oxidation of Longifolene to Isolongifolol

A convenient one-pot hydroboration / isomerization / oxidation of longifolene (1) to the thermodynamically more stable epimer, isolongifolol (3) is described.Furthermore, a practical in situ method for the hydroboration of 1 in THF, has been optimised to generate the less stable epimer, longifolol (2).