93379-48-7

Usage

Uses

Used in Asymmetric Catalysis:
(-)-Taddol is used as a hydrogen-bonding organocatalyst for various applications in asymmetric catalysis. Its strong hydrogen-bonding ability and chiral structure make it an effective catalyst in promoting enantioselective reactions.
Used in the Synthesis of Cyclopropylamines:
(-)-Taddol is used as a reactant or reagent in the synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides. This process allows for the formation of cyclopropylamines with high enantioselectivity, which are important building blocks in the synthesis of pharmaceuticals and agrochemicals.
Used in Enantioswitching of Catalytic Asymmetric Hydroboration:
(-)-Taddol is employed as a catalyst in the enantioswitching of catalytic asymmetric hydroboration. This process enables the selective formation of one enantiomer over the other, which is crucial for the production of enantiomerically pure compounds.
Used in the Synthesis of Derivative Ligands for Asymmetric Hydroformylation:
(-)-Taddol is used as a reactant or reagent in the synthesis of derivative ligands for asymmetric hydroformylation of alkenes. These ligands play a vital role in enhancing the enantioselectivity and efficiency of the hydroformylation process.
Used in Amide-Directed Catalytic Asymmetric Hydroboration of Trisubstituted Alkenes:
(-)-Taddol is utilized as a catalyst in the amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes. This method allows for the selective formation of enantioenriched products, which are valuable intermediates in the synthesis of complex organic molecules.
Used in the Addition of Deactivated Alkyl Grignard Reagents to Aldehydes:
(-)-Taddol is used as a catalyst in the addition of deactivated alkyl Grignard reagents to aldehydes. This process enables the formation of alcohols with high enantioselectivity, which are important for the synthesis of biologically active compounds and pharmaceuticals.

InChI:InChI=1/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1

Upstream product

• 108-86-1 bromobenzene 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 77-76-9 2,2-dimethoxy-propane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 100-58-3 phenylmagnesium bromide 
• 195449-36-6 Pent-4-enoic acid (R)-7-oxo-1-pentyl-heptyl ester 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 

Downstream Products

• 144109-23-9 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with methanol 
• 126524-76-3 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with propylamine 
• 126525-04-0 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with tripropyl-amine 
• 213843-95-9 1-((3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine-6-yl)piperidine 
• 1192678-82-2 (3aR,8aR)-(-)-(2,2-dimethyl-4,4,8,8-tetraphenyl-tetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-yl)dimethylamine 
• 1352731-41-9 C₃₃H₂₈N₂O₂ 

Relevant academic research and scientific papers

Asymmetric ozone oxidation of silylalkenes using a C2- symmetrical dialkoxysilyl group as a chiral auxiliary

Ozone oxidation of silyl-substituted alkenes, namely silylalkenes, proceeds in an addition-type manner to afford α-silylperoxy carbonyl compounds in good to excellent yields, without the formation of normal ozonolysis products. Herein the ozone oxidation

Highly enantioselective nickel-catalyzed hydrocyanation of disubstituted methylenecyclopropanes enabled by taddol-based diphosphite ligands

A vast range of novel TADDOL-based diphosphite ligands were first synthesized and applied in the nickel-catalyzed asymmetric hydrocyanation of disubstituted methylenecyclopropanes. By employing these new catalysts, the conversion of diverse methylenecyclo

Chiral Aluminum Complex Controls Enantioselective Nickel-Catalyzed Synthesis of Indenes: C?CN Bond Activation

A chiral aluminum complex controlled, enantioselective nickel-catalyzed domino reaction of aryl nitriles and alkynes proceeding by C?CN bond activation was developed. The reaction provides various indenes, bearing chiral all-carbon quaternary centers, under mild reaction conditions in yields of 32 to 91 percent and ee values within the 73–98 percent range. The reaction mechanism and aspects of stereocontrol were investigated by DFT calculations.

Phosphite-Catalyzed C?H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement

A phosphite-mediated [2,3]-aza-Wittig rearrangement has been developed for the regio- and enantioselective allylic alkylation of six-membered heteroaromatic compounds (azaarenes). The nucleophilic phosphite adducts of N-allyl salts undergo a stereoselective base-mediated aza-Wittig rearrangement and dissociation of the chiral phosphite for overall C?H functionalization of azaarenes. This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both the allyl part and azaarenes. Catalysis with chiral phosphites is also demonstrated with synthetically useful yields and enantioselectivities.

Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs

Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.

Enantioselective Direct Synthesis of syn- and anti-α,β-Dihydroxy γ-Keto Esters Using a Dinuclear Zinc–AzePhenol Complex

A one-step enantioselective direct synthesis of both syn- and anti-α,β-dihydroxy γ-keto esters using a dinuclear zinc–AzePhenol complex is presented. This asymmetric α-hydroxyacetate aldol reaction proceeds in moderate to good yield and with excellent ena

An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.

Enantioselective Ni-Al Bimetallic Catalyzed exo -Selective C-H Cyclization of Imidazoles with Alkenes

A Ni-Al bimetallic catalyzed enantioselective C-H exo-selective cyclization of imidazoles with alkenes has been developed. A series of bi- or polycyclic imidazoles with β-stereocenter were obtained in up to 98% yield and >99% ee. The bifunctional SPO ligand-promoted bimetallic catalysis proved to be critical to this challenging stereocontrol.

Chiral Phosphine–Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition

The AuI-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions.

Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)?H Carbamoylation

A general and user-friendly synthesis of β-lactams is reported that makes use of Pd0-catalyzed carbamoylation of C(sp3)?H bonds, and operates under stoichiometric carbon monoxide in a two-chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C?H bonds, in contrast to previous methods based on C(sp3)?H activation. In addition, the feasibility of an enantioselective version using a chiral phosphonite ligand is demonstrated. Finally, this method can be employed to synthesize valuable enantiopure free β-lactams and β-amino acids.