50778-41-1

Upstream product

• 555-31-7 aluminum isopropoxide 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 123-38-6 propionaldehyde 
• 74-96-4 ethyl bromide 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 925-90-6 ethylmagnesium bromide 
• 557-20-0 diethylzinc 

Downstream Products

• 1360592-70-6 1-cyclohexenylpropyl 2-(diphenylphosphanyl)benzoate 
• 1655-03-4 1-cyclohex-1-enyl-propan-1-one 
• 185758-52-5 (R)-1-cyclohexenylpropan-1-ol 
• 110529-28-7 (S)-1-cyclohexylpropan-1-ol 

Relevant academic research and scientific papers

Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C-H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines

Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a ki

Nickel-Catalyzed Highly Selective Hydroalkenylation of Alkenyl Boronic Esters to Access Allyl Boron

Allyl boron derivatives are valuable building blocks in the synthesis of natural products and bioactive molecules. Herein, a practical strategy of nickel-catalyzed highly selective hydroalkenylation of alkenyl boronic esters was developed. Under the mild

Nazarov cyclization of divinyl ketones bearing an ester group at the β-position: A remarkable effect of α-substitution and alkene geometry on regioselectivity

The Nazarov cyclization of divinyl ketones with an ester at the β-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the subtle substitution patterns at the α-position and alkene geometry of α,β and mostly, this selectivity is regardless of substitutions at α′- and β′-positions. The major implications of these observations are an aromatic group at the α-position with E-olefin geometry provides a cyclopentenone in which the double bond is not in conjugation with an ester, whereas Z-olefin provides a cyclopentenone in which the double bond is in conjugation with an ester; and divinyl ketones bearing an ester group at the β-position and an alkyl group at the α-position with E-olefin geometry provide a cyclopentenone in which the double bond is in conjugation with the ester.

Stereoselective synthesis of trisubstituted olefins by a directed allylic substitution strategy

New methodology for the stereoselective synthesis of trisubstituted olefins is presented. The use of ortho-diphenylphosphanyl benzoate (o-DPPB) as a directing leaving group for copper-mediated allylic substitution with Grignard reagents allowed for the stereoselective construction of a wide range of E olefins, without the need for an adjacent electron-withdrawing group. Our modular three-step approach toward trisubstituted alkenes commenced with geminal α-methylene aldehydes. Addition of an organometallic reagent and introduction of the o-DPPB group by esterification was followed by the o-DPPB-directed copper-mediated allylic substitution with a Grignard reagent to furnish stereodefined trisubstituted olefins. Additionally, incorporation of a stereocenter from the chiral pool allowed the preparation of an enantiomerically pure olefin that bore three alkyl substituents in high E/Z selectivity.

Copper-catalyzed enantioselective 1,4-addition to α,β- unsaturated aldehydes

Figure presented The first asymmetric Cu-catalyzed conjugate addition of dialkylzinc zinc reagents to a large scope of enals in presence of phosphoramidite, SimplePhos, or (R)-BINAP ligands with enantiomeric excesses up to 90% is reported. Moreover, ACA of Grignard reagents afforded moderate to good 1,4-regioselectivities with enantioselectivities up to 90%.