138602-95-6

Upstream product

• 6305-59-5 ethyl 3-hydroxy-3-cyclohexyl-2-methylpropanoate 
• 79-03-8 propionyl chloride 
• 2043-61-0 cyclohexanecarbaldehyde 
• 138490-39-8 (2S*,3R*)-3-(tert-butyldimethylsilyloxy)-3-cyclohexyl-2-methylpropanol 
• 138490-38-7 (+/-)-3-(tert-butyldimethylsilyloxy)-3-cyclohexyl-2-methyl-1-propene 
• 138490-37-6 (±)-1-cyclohexyl-2-methylprop-2-en-1-ol 
• 135067-18-4 (1R*,2S*)-1-cyclohexyl-2-methyl-1,3-bis(trimethylsiloxy)propane 

Downstream Products

• 79388-54-8 2-Cyclohexyl-3-methyl-oxetane 
• 1047670-90-5 (4S,5R)-2,2,5-trimethyl-4-cyclohexyl-[1,3]-dioxane 
• 138604-11-2 (2R,3S,6S,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138490-36-5 (2S,3R,6R,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138490-36-5 (2R,3S,6S,7R,10S)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 138490-36-5 (2R,3S,6S,7S,10R)-2-Cyclohexyl-7-isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undecane 
• 105401-07-8 (1R,2S)-1-cyclohexyl-2-methyl-1,3-propanediol 
• 135067-18-4 (1R*,2S*)-1-cyclohexyl-2-methyl-1,3-bis(trimethylsiloxy)propane 
• 138603-03-9 (2R,3R)-3-Cyclohexyl-3-hydroxy-2-methyl-propionic acid 
• 138490-51-4 (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal 
• 78604-73-6 (-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate 

Relevant academic research and scientific papers

Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols

An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).

Rapid and stereochemically flexible synthesis of polypropionates: Super-silyl-governed aldol cascades

Polypropionates made EZ: The E/Z geometry of tris(trimethylsilyl)silyl super silyl enol ethers derived from propionaldehyde controls diastereoselectivity in the aldehyde crossed-aldol reaction. These silyl enol ethers can participate in polyaldol cascade reactions, thus allowing the one-pot synthesis of four different dipropionate stereotetrads (see scheme), and polyketides bearing up to five contiguous stereocenters.

Combined proline-surfactant organocatalyst for the highly diastereo- and enantioselective aqueous direct cross-aldol reaction of aldehydes

(Chemical Equation Presented) Why not combine the two? The asymmetric direct aldol reaction of two different aldehydes was catalyzed by a combined proline-surfactant organic catalyst in the presence of water. A stable emulsion was formed in the reaction mixture, and the aldols were obtained with excellent diastereo- and enantioselectivities (see scheme).

Aldol reactions on solid phase. Sc(OTf)3-catalyzed aldol reactions of polymer-supported silyl enol ethers with aldehydes providing convenient methods for the preparation of 1,3-diol, β-hydroxy carboxylic acid, and β-hydroxy aldehyde libraries

Aldol reactions on solid phase have been achieved. In the presence of a catalytic amount of scandium triflate (Sc(OTf)3), polymer-supported silyl enol ethers reacted with aldehydes to afford the corresponding β-hydroxy thioester derivatives, which were reduced to 1,3-diol and β-hydroxy aldehyde derivatives, or hydrolyzed to β-hydroxy carboxylic acid derivatives.

BCl3- and TiCl4-mediated reductions of β-hydroxy ketones

Syn-selective reduction protocols for β-hydroxy ketones are described exploiting the intermediacy of titanium and boron chelates derived from TiCl4 and BCl3, respectively. Reductions are conducted at -78°C in CH2Cl2/

Stereoselective Acetalization of 1,3-Alkanediols by l-Menthone: Application to the Resolution of Racemic 1,3-Alkanediols and to the Determination of the Absolute Configuration of Enantiomeric 1,3-Alkanediols

A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described.Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4.The two can be readily separated by silica gel column chromatography.Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol.An empirically derived correlation of configuration and 1H NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation.The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

Enantioselective acetalization of racemic 1,3-alkanediols with l-methone under kinetically controlled conditions

Racemic 1,3-alkanediols (rac-1) undergo an enantioselective acetalization by treatment with l-methone enol trimethylsilyl ether (10) in the presence of trifluoromethanesulfonic acid (10 mol%) to give thermodynamically less stable spiroacetal 3 (derived fr