61198-49-0

Upstream product

• 4160-80-9 3-phenylglutaric acid anhydride 
• 128951-26-8 6-Methylsulfanyl-4-phenyl-pyran-2-one 
• 624-76-0 Iodoethanol 
• 109299-93-6 3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one 
• 173909-83-6 (3-phenylacryloyl)benzamide 
• 37612-74-1 (E)‐1‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐3‐phenylprop‐2‐en‐1‐one 
• 3393-45-1 5,6-dihydro-pyran-2-one 
• 98-80-6 phenylboronic acid 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 1352708-09-8 trimethyl((5-methyl-2-phenyl-1,3,2-dioxaborinan-5-yl)methoxy)silane 
• 52205-01-3 (5-methyl-2-phenyl-[1,3,2]dioxaborinan-5-yl)-methanol 
• 591-51-5 phenyllithium 
• 591-50-4 iodobenzene 
• 829-27-6 3-phenylpentane-1,5-diol 

Downstream Products

• 69815-04-9 (+/-)-5-Methyl-3-phenyl-1,5-hexandiol 
• 58068-76-1 2-hydroxy-4-phenyltetrahydropyran 
• 114199-69-8 2-ethyl-3-phenyl-5-pentanolide 
• 114199-68-7 2-methyl-3-phenyl-5-pentanolide 
• 71302-21-1 (4R)-4-phenyltetrahydro-2H-pyran-2-one 
• 790661-97-1 trifluoromethanesulfonic acid 4-phenyl-5,6-dihydro-4H-pyran-2-yl ester 
• 861818-42-0 7-oxo-5-phenyl-hept-2-enoic acid ethyl ester 
• 861818-39-5 7-hydroxy-5-phenyl-hept-2-enoic acid ethyl ester 
• 790661-98-2 (E)-6-(1-ethoxybuta-1,3-dienyl)-4-phenyl-3,4-dihydro-2H-pyran 
• 790662-00-9 5-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one 
• 790662-00-9 5-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one 
• 188670-33-9 7-Hydroxy-2-methyl-5-phenyl-heptanoic acid ethyl ester 
• 188670-37-3 7-Bromo-2-methyl-5-phenyl-heptanoic acid ethyl ester 
• 114199-65-4 2-methylene-3-phenyl-5-pentanolide 

Relevant academic research and scientific papers

Asymmetric Synthesis of Chiral Bicyclo[2.2.1]hepta-2,5-diene Ligands through Rhodium-Catalyzed Asymmetric Arylative Bis-cyclization of a 1,6-Enyne

A series of novel chiral diene ligands (1R,4S)-L1, which are based on the bicyclo[2.2.1]heptadiene skeleton and are substituted with methyl and an ester group at the bridgehead carbons, were synthesized through rhodium-catalyzed asymmetric arylative bis-c

New Access Routes to Privileged and Chiral Ligands for Transition-Metal Catalyzed Hydrogen Autotransfer (Borrowing Hydrogen), Dehydrogenative Condensation, and Alkene Isomerization Reactions

A group of transition-metal catalyzed hydrogen moving reactions, encompassing hydrogen autotransfer (HAT; also called borrowing hydrogen, BH), dehydrogenative condensation (DHC) and alkene isomerization, displays high atom economy and relies on widely ava

Tricyclic Sulfoxide-Alkene Hybrid Ligands for Chiral Rh(I) Complexes: The "Matched" Diastereomer Catalyzes Asymmetric C-C Bond Formations

Deprotonation of phenyldibenzo[b,f]tropylidene (8) with LDA/t-BuOK followed by quenching with either diastereomer of inexpensive glucose-based t-Bu-sulfinate (R)- or (S)-11 affords a sulfoxide-alkene hybrid ligand as the diastereomeric pairs (SS,SC)-9/(SS,RC)-10 and (RS,RC)-9/(RS,SC)-10, respectively, which via chromatographic/recrystallization may be separated into the four isomers. The optically pure diastereomeric ligands (SS,SC)-9 and (SS,RC)-10 react with [RhCl(coe)2]2 to form the dinuclear complexes (RS,SC)-11 and (RS,RC)-12, respectively, in which the bidentate ligands coordinate the metal centers through the sulfur and alkene donor functions. These complexes catalyze the conjugate addition of arylboronic acids to cyclic Michael acceptors with enantioselectivities of up to 99% ee. DFT calculations show the preponderant influence of planar chirality of the ligand alkene function. The enantioselectivity switch observed between (RS,SC)-11 and (RS,RC)-12 is explained by the inverted cis-trans coordinations of the substrate molecules in catalytic steps.

The mutagenesis of a single site for enhancing or reversing the enantio- or regiopreference of cyclohexanone monooxygenases

The mutagenesis of a "second sphere"switch residue of CHMOAcineto could control its enantio- and regiopreference. Replacing phenylalanine (F) at position 277 of CHMOAcineto into larger tryptophan (W) enabled a significant enhancement of enantio- or regioselectivity toward structurally diverse substrates, moreover, a complete reversal of enantio- or regiopreference was realized by mutating F277 into a range of smaller amino acids (A/C/D/E/G/H/I/K/L/M/N/P/Q/R/S/T/V).

Control of Enantioselectivity in Rhodium(I) Catalysis by Planar Chiral Dibenzo[a,e]cyclooctatetraenes

Planar chiral 5,11-disubstiuted dibenzo[a,e]cyclo-octatetraenes (dbCOTs) have been developed as the first useful chiral homologs to dbCOT-ligands for asymmetric applications. Methods enabling the preparation of such compounds on a gram-scale in enantiomerically pure form are described. Evaluated as ligands in rhodium(I)-catalyzed 1,4- and 1,2-arylation reactions, tertiary and quarternary stereogenic centers were formed with excellent yields and selectivities of up to >99 % ee. A catalytic asymmetric synthesis of a key cyclization precursor to (?)-penifulvin A highlights the system in an applied context.

Aqueous Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex under Batch and Continuous-Flow Conditions

A rhodium-chiral diene complex immobilized on amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin (PS-PEG-diene?-Rh) has been developed. The immobilized rhodium-chiral diene complex (PS-PEG-diene?-Rh) efficiently catalyzed the asymmetric 1,4-addition of various arylboronic acids to cyclic or linear enones in water under batch conditions to give the corresponding β-arylated carbonyl compounds in excellent yields and with excellent enantioselectivity. The catalyst was readily recovered by simple filtration and reused 10 times without loss of its catalytic activity and enantioselectivity. Moreover, a continuous-flow asymmetric 1,4-addition in a flow reactor containing PS-PEG-diene?-Rh proceeded efficiently at 50 °C with retention of high enantioselectivity. Long-term continuous-flow asymmetric 1,4-addition during 12 h readily gave the desired product on a 10 g scale with high enantioselectivity.

Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cpa? -Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions.

Enantioselective preparation of δ-valerolactones with horse liver alcohol dehydrogenase

Horse liver alcohol dehydrogenase (HLADH) has been found to be a versatile biocatalyst for the desymmetrization of prochiral 3-arylpentane-1,5-diols, based on a two-step one-pot oxidation. This procedure has allowed the formation of valuable (S)-lactones in good to excellent conversions and enantiomeric excess. The catalytic performance of HLADH has been studied using several cofactor regeneration systems and cosolvents, finding great improvements in terms of activity with L-lactate dehydrogenase, while the stereoselectivity of the process was significantly improved when using tetrahydrofuran. Docking studies has revealed the pattern substitution importance in the selectivity and activity of this oxidative process. Not just horsing around: Horse liver alcohol dehydrogenase is found to be a versatile biocatalyst for the desymmetrization of 3-arylpentane-1,5-diols through a two-step one-pot oxidation. The catalytic performance of horse liver alcohol dehydrogenase (HLADH) is studied with several cofactor regeneration systems and cosolvents. Docking studies reveal the importance of pattern substitution in the selectivity and activity of this biotransformation.

Phosphine-olefin ligands based on a planar-chiral (π-Arene)chromium scaffold: Design, synthesis, and application in asymmetric catalysis

The NMR and X-ray crystallographic studies clarified that planar-chiral alkenylene-bridged (phosphino-π-arene)(phosphine)chromium complexes 3 were capable of coordinating to a rhodium(I) cation in a bidentate fashion at the (π-arene)-bound phosphorus atom

Chiral porous organic frameworks for asymmetric heterogeneous catalysis and gas chromatographic separation

Three chiral robust diene-based porous organic frameworks (POFs) are prepared. POF-1 is shown to be an efficient heterogeneous catalyst after metallation for asymmetric conjugation addition with up to 93% ee, and it can also function as a new chiral stationary phase for gas chromatographic separation of racemates. This journal is