6305-59-5

Upstream product

• 77642-81-0 ethyl 3-cyclohexyl-2,3-epoxy-2-methylpropanoate 
• 105-37-3 Ethyl propionate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 535-11-5 Ethyl 2-bromopropionate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 71911-66-5 ethyl α-methyl-β-oxocyclohexanepropanoate 

Downstream Products

• 71911-66-5 ethyl α-methyl-β-oxocyclohexanepropanoate 
• 105401-07-8 1-cyclohexyl-2-methyl-1,3-propane diol 
• 6305-59-5 (2S,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-propionic acid ethyl ester 
• 6305-59-5 (2R,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Manganese-promoted regioselective ring-opening of 2,3-epoxy acid derivatives: a new route to α-hydroxy acid derivatives

A simple and general methodology directed towards the synthesis 3-aryl-2-hydroxy amides, or esters with total regioselectivity from the easily available 2,3-epoxy amides or esters, promoted by active manganese is described. Utilizing enantiopure epoxy amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.

An efficient cobalt(I)-catalysed reformatsky reaction using α-chloro esters

An efficient cobalt(I)-catalysed Reformatsky reaction using α-chloro esters has been developed. The catalyst is prepared by reducing the cobalt(II) chloride (5%)/1,2-bis(diphenylphosphino)ethane (dppe)(5%)/zinc iodide (10%) system with zinc metal in acetonitrile in the presence of both the α-chloro ester and the carbonyl compound; good to excellent conversions to β-hydroxy esters are obtained at room temperature in 2.5 h.

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/

Low-valent Tantalum-mediated Reaction

Treatment of a mixture of α-halogeno-esters and carbonyl compounds with low valent tantalum prepared readily from tantalum(V) chloride and activated zinc, afforded β-hydroxy esters in moderate to good yields.

Stereoselective reduction of 2-methyl-3-oxo esters (or amides) with sodium borohydride catalyzed by manganese (II) chloride or tetrabutylammonium borohydride. A practical preparation of erythro and threo-3-hydroxy-2-methyl esters (or amides)

erythro-3-Hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 2-methyl-3-oxo esters or 2-methyl-3-oxo amides in the presence of a catalytic amount of manganese(II) chloride. On the other hand, reduction of these substrates with n-Bu4NBH4 provided threo-isomers selectively. erythro-Selective reduction of 2-methyl-3-oxo amides with NaBH3CN in 1N HCl-MeOH is also described.

A PRACTICAL AND STEREOSELECTIVE REDUCTION OF 3-KETO-2-METHYL ESTERS OR 3-KETO-2-METHYL AMIDES INTO ERYTHRO-3-HYDROXY-2-METHYL ESTERS OR ERYTHRO-3-HYDROXY-2-METHYL AMIDES WITH NaBH4 CATALYZED BY MnCl2

Erythro-3-hydroxy-2-methylpropionates or erythro-3-hydroxy-2-methylpropionamides were prepared with high stereoselectivity by NaBH4 reduction of the corresponding 3-keto esters or 3-keto amides in the presence of a catalytic amount of MnCl2.

SmI2-INDUCED HIGHLY REGIOSELECTIVE REDUCTION OF α,β-EPOXY ESTERS AND γ,δ-EPOXY-α,β-UNSATURATED ESTERS. AN EFFICIENT ROUTE TO OPTICALLY ACTIVE β-HYDROXY AND δ-HYDROXY ESTERS

α,β-Epoxy esters were rapidly reduced at room temperature to yield β-hydroxy esters with retention of the configurations at the β-carbon atoms by using SmI2-THF-HMPA system in the presence of N,N-dimethylaminoethanol (DMAE).The conditions were successfully applied to the synthesis of vinylogous δ-hydroxy esters.