113829-97-3

Upstream product

• 930-68-7 cyclohexenone 
• 134880-11-8 (4S)-1-methyl-4,5,6,7-tetrahydro-4-phenyl-2,1-benzisoxazolin-3-one 
• 591-51-5 phenyllithium 
• 1728-18-3 dimethylacetal of cyclohexenone 
• 100-58-3 phenylmagnesium bromide 
• 115880-50-7 (R)-2-phenoxypropanoic acid methyl ester 
• 396718-95-9 [(R)-3-Phenyl-cyclohex-(E)-ylidene]-acetaldehyde 
• 1078-58-6 diphenylzinc 
• 98-80-6 phenylboronic acid 
• 3262-89-3 triphenylboroxine 
• 16419-60-6 2-Methylphenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 960-71-4 triphenylborane 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 76936-85-1 (+)-(R)-3-phenyl-1-(2-tolyl)cyclohexene 
• 1232059-66-3 C₁₃H₁₆O₂ 
• 1232059-68-5 (1R,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-56-1 C₁₃H₁₅N 
• 1232059-70-9 (1S,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-79-8 C₁₃H₁₉N 

Relevant academic research and scientific papers

First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach

(Matrix presented) Using a combination of chiral monodentate phosphoramidite ligands in the rhodium-catalyzed conjugate addition of boronic acids to three different substrates, we have shown for the first time that the ligand combination approach is applicable for C-C bond formation. Chiral catalysts based on hetero-combinations of ligands are found to be more effective than the homo-combinations, 31P NMR experiments show that the hetero-combinations are formed in excess over the homo-combinations.

Synthesis of atropisomeric chiral MeOBIPHEP analogues via Pd-catalyzed P-C coupling - applications to asymmetric Rh-catalyzed C-C bond formations in water

Abstract The preparation and catalytic applications of water-soluble MeOBIPHEP-based atropisomeric chiral congener ligands are described. The optimization of the catalytic system to promote the key P-C coupling revealed the superiority of palladium cataly

Synthesis, Characterization, and Application of Segphos Derivative Having Diferrocenylphosphino-Donor Moieties

An axially chiral bisphosphine, Fc-Segphos (1), which possesses diferrocenylphosphino-donor moieties, was prepared as a racemate, and its optical resolution was achieved by the use of chiral HPLC. Ligand 1 coordinated to a palladium(II) cation in a bidentate fashion to construct a unique chiral environment at the palladium center due to the sterically demanding ferrocenyl groups. Ligand (R)-1 was applied in the palladium-catalyzed asymmetric synthesis of axially chiral allenes showing good enantioselectivity of up to 92% ee. In general, (R)-1 displayed better enantioselectivity than the parent Segphos in the palladium-catalyzed reaction, and the Pd/(R)-1 species showed up to 18% ee enhancement over the (R)-Segphos-derived palladium catalyst.

Asymmetric addition of phenylboronic acid to cycloalkanones mediated by a Rh/phosphoramidite complex: A comparison between tropos versus nontropos behavior

Herein we report the asymmetric addition of phenylboronic acid to different cycloalkenones, mediated by a Rh(I) complex with the tropos phosphoramidite (S)-L1 or the nontropos phosphoramidite (S)-L2 ligand. Different values of enanti

Steric Tuning of Sulfinamide/Sulfoxides as Chiral Ligands with C1, Pseudo-meso, and Pseudo-C2 Symmetries: Application in Rhodium(I)-Mediated Arylation

A new family of sulfinamide/sulfoxide derivatives was synthesized as chiral bidentate ligands by stereoselective additions of methylsulfinyl carbanions to N-tert-butylsulfinylimines. The new ligands, with C1, pseudo-meso, and pseudo-C2 symmetries, were successfully assayed in Rh-catalyzed additions of arylboronic acids to activated ketones. The sterically dissymmetric C1 ligand (RS,SC,RS)-N-[1-(phenylsulfinyl)-3-methylbut-2-yl] tert-butylsulfinamide turned out to be the optimal one, allowing the 1,4-additions of diverse arylboronic acids, on different α,β-unsaturated cyclic ketones with high chemical yields and enantioselectivities up to >99% ee.

A short synthesis of (+)-β-lycorane by asymmetric conjugate addition cascade

Abstract The chiral diether ligand-controlled asymmetric conjugate addition of organolithiums to nona-2,7-dienedioate and subsequent intramolecular conjugate addition of the enolate intermediate gave all-trans trisubstituted cyclohexanes with high ee and

Enantioselective palladium-catalysed conjugate addition of arylsiloxanes

The complex formed from Pd(CH3CN)4(BF 4)2 and (R,R)-MeDUPHOS is a highly enantioselective catalyst for the asymmetric conjugate addition of aryltriethylsiloxanes to a variety of unsaturated ketones, lactones and

Construction of axial chirality by rhodium-catalyzed asymmetric dehydrogenative heck coupling of biaryl compounds with alkenes

Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C-H bond olefination of biaryl compounds, using a chiral [CpRhIII] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions.

Synthesis of novel chiral phosphine-olefin complexes and their evaluation as ligands in the rhodium-catalyzed asymmetric 1,4-addition

Novel chiral phosphine-olefin complexes containing ferrocene and cyrhetrene backbones have been synthesized and evaluated as ligands in the rhodium-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone. The highest efficiency in this series was ob

Simple oxazolidine chiral diene ligands for enantioselective rh-catalyzed conjugate additions

Simple oxazolidine-based chiral diene ligands, ultimately derived from serine, have been synthesized using the Seebach self-regeneration of stereocenters strategy. The ligands have been used in the enantioselective Rh-catalyzed conjugate addition of aryl