28637-53-8

Upstream product

• 108-24-7 acetic anhydride 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 29569-79-7 ethyl (1S,2S)-2-hydroxycyclohexanecarboxylate 
• 61586-78-5 ethyl (1R,2S)-2-hydroxycyclohexane-1-carboxylate 
• 1192306-31-2 ethyl 2-hexylcyclohex-1-enecarboxylate 
• 1192306-33-4 ethyl 2-dodecylcyclohex-1-enecarboxylate 
• 38504-00-6 ethyl 2-phenethylcyclohex-1-enecarboxylate 
• 104654-69-5 Ethyl 2-methyl-1-cyclohex-1-ene carboxylate 
• 1192306-38-9 ethyl 2-(6-(tetrahydro-2H-pyran-2-yloxy)hexyl)cyclohex-1-enecarboxylate 
• 173277-75-3 ethyl 3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 

Relevant academic research and scientific papers

Reduction of acyl enolates of alpha-substituted beta-keto esters by bakers' yeast.

Enol esters of 2-substituted-3-oxoalkanoates of (Z)-configuration were reduced by bakers' yeast to chiral 2-substituted-3-hydroxyalkanoates. The syn-selectivities of this reaction increased compared with those of the reduction of the corresponding racemic

Chromium(II)-Catalyzed Diastereoselective and Chemoselective Csp2-Csp3 Cross-Couplings Using Organomagnesium Reagents

A simple protocol for performing chromium-catalyzed highly diastereoselective alkylations of arylmagnesium halides with cyclohexyl iodides at ambient temperature has been developed. Furthermore, this ligand-free CrCl2 enables efficient electrophilic alkenylations of primary, secondary, and tetiary alkylmagnesium halides with readily available alkenyl acetates. Moreover, this chemoselective C-C coupling reaction with stereodefined alkenyl acetates proceeds in a stereoretentive fashion. A wide range of functional groups on alkyl iodides and alkenyl acetates are well tolerated, thus furnishing functionalized Csp2-Csp3 coupling products in good yields and high diastereoselectivity. Detailed mechanistic studies suggest that the in situ generated low-valent chromium(I) species might be the active catalyst for these Csp2-Csp3 cross-couplings.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.