40412-38-2

Upstream product

• 80441-31-2 (SS)-1-cyclohexyl-2-(N-methylphenylsulfonimidoyl)-1-phenylethanol 
• 1078-58-6 diphenylzinc 
• 823-76-7 Cyclohexyl methyl ketone 
• 712-50-5 Cyclohexyl phenyl ketone 
• 917-64-6 methyl magnesium iodide 
• 157994-11-1 (+/-)-1-cyclohexyl-1-phenyleth-1-yl hydroperoxide 
• 1240815-89-7 (S)-2-(1-cyclohexyl-1-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 313374-39-9 ethylphenylzinc 
• 98-86-2 acetophenone 
• 931-50-0 cyclohexylmagnesium bromide 
• 100-58-3 phenylmagnesium bromide 
• 4352-39-0 1-cyclohexyl-1-phenylethanol 
• 789-25-3 HSiPh₃ 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

A new aspect of magnesium bromide-promoted enantio-selective aryl additions of triaryl(tetrahydrofuran)aluminum to ketones catalyzed by a titanium(IV) catalyst of trans-1,2-bis(hydroxycamphorsulfonylamino)cyclohexane

A novel aspect of MgBr2-promoted asymmetric triarylaluminum- tetrahydrofuran [AlAr3 (THF)] additions to ketones catalyzed by a titanium catalyst of 20 mol% trans-1,2-bis(hydroxycamphorsulfonylamino) cyclohexane (2) is reported. The catalytic system works excellently for aromatic ketones with either an electron-withdrawing or an electrondonating substituent on the aromatic ring at the 2′-, 3′-, or 4′-positions, affording tertiary alcohols in excellent enantioselectivities of ≥90% ee, except for the cases of phenyl addition to 2′-methoxyacetophenone and 4-trimethylsilylphenyl (4-TMSC6H4) addition to acetopheneone.

Highly enantioselective catalytic phenylation of ketones with a constrained geometry titanium catalyst

(Matrix Presented) The catalytic asymmetric addition of phenyl groups from diphenylzinc to ketones is reported. The catalyst, generated from a dihydroxy bis-(sulfonamide) ligand and titanium tetraisopropoxide, gives good to excellent enantioselectivities with a range of substrates.

Fast Enantio- and Chemoselective Arylation of Ketones with Organoboronic Esters Enabled by Nickel/N-Heterocyclic Carbene Catalysis

A general, efficient, highly enantio- and chemoselective N-heterocyclic carbene (NHC)/Ni-catalyzed addition of readily available and stable arylboronic esters to ketones is reported. This protocol provides unexpectedly fast access (usually 10 min) to various chiral tertiary alcohols with exceptionally broad substrate scope and excellent functional group tolerance (76 examples, up to 98 % ee). This process is orthogonal to other known Ni-mediated Suzuki–Miyaura couplings, as it tolerates aryl chlorides, fluorides, ethers, esters, amides, nitriles, and alkyl chlorides. The reaction is applied to late-stage modifications of various densely functionalized medicinally relevant molecules. Preliminary mechanistic studies suggest that a rare enantioselective η2-coordinating activation of ketone carbonyls is involved. This cross-coupling-like mechanism is expected to enable other challenging transformations of ketones.

Enantioconvergent Arylation of Racemic Secondary Alcohols to Chiral Tertiary Alcohols Enabled by Nickel/N-Heterocyclic Carbene Catalysis

The direct upgrading reaction of simple and readily available achiral alcohols via C-H functionalization is an ideal strategy to prepare value-added chiral higher alcohols. Herein, we disclose the first enantioconvergent upgrading reaction of simple racemic secondary alcohols to enantioenriched tertiary alcohols. An N-heterocyclic carbene (NHC)-nickel catalyst was leveraged to enable this highly efficient formal asymmetric alcohol α-C-H arylation via a dehydrogenation using phenyl triflate as a mild oxidant followed by asymmetric addition of arylboronic esters to the transient ketones. Mechanistic studies and control experiments were conducted to reveal the possible reasons for the exceptional control over chemo- and enantioselectivity.

Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the naphthyl requirement that pervades stereospecific cross-couplings involving enantioenriched electrophiles.

Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu?H-Catalyzed Si?O Coupling

A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst-controlled enantioselective silylation. This non-enzymatic kinetic resolution is catalyzed by a Cu?H species and makes use of the commercially available precatalyst MesCu/(R,R)-Ph-BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl- as well as dialkyl-substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post-functionalization in this position (s up to 207).

Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones

The enantioselective addition of Grignard reagents to ketones was promoted by a BINOL derivative bearing alkyl chains at the 3,3′-positions. This is the first asymmetric direct aryl Grignard addition to ketones reported to date. A variety of tertiary diaryl alcohols could be obtained in high yields and enantioselectivities without using any other metal source.

Zn(salen)-catalyzed enantioselective phenyl transfer to aldehydes and ketones with organozinc reagent

Abstract A chiral zinc complex of salen was found to be an efficient catalyst for the phenyl transfer of organozinc reagent to aromatic aldehydes and ketones. High enantioselectivities were obtained in reactions of both aromatic aldehydes and ketones (up to 97% and 92% ee, respectively).

Full chirality transfer in the conversion of secondary alcohols into tertiary boronic esters and alcohols using lithiation-borylation reactions

New conditions, full transfer: Using MgBr2/MeOH as an additive now provides essentially 100 % retention of configuration in the lithiation-borylation reaction, thus leading to tertiary boronic esters (or tertiary alcohols) with exceptionally hi

PHOSPHOROAMIDE COMPOUND, METHOD FOR PRODUCING THE SAME, LIGAND, COMPLEX, CATALYST, AND METHOD FOR PRODUCING OPTICALLY ACTIVE ALCOHOL

Disclosed is a method for highly efficiently obtaining an optically active alcohol from a carbonyl compound highly enantioselectively. Also disclosed is a ligand used in such a method. Specifically, an optically active alcohol is obtained by reacting a ca