93379-48-7

Basic information

• Product Name: (-)-Taddol
• Synonyms: (4R,5R)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE;(4R,5R)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-DIOXOLANE;(-)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2,2-DIMETHYL-1,3-DIOXOLANE;(R,R)-TADDOL;(R,R)-(-)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-L-THREITOL;(-)-TADDOL;TADDOL;SEEBACH REAGENT
• CAS NO: 93379-48-7
• Molecular Formula: C₃₁H₃₀O₄
• Molecular Weight: 466.57
• Product Categories: chiral;Asymmetric Synthesis;Biochemistry;Dioxanes & Dioxolanes;Dioxolanes;O-Substituted Sugars;Sugar Alcohols;Sugars;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Chiral Oxygen;TADDOL Series
• Mol File: 93379-48-7.mol
• Article Data: 27

Chemical Properties

• Melting Point: 193-195 °C(lit.)
• Boiling Point: 489.39°C (rough estimate)
• Flash Point: 336.7 °C
• Appearance: white/Powder
• Density: 1.0864 (rough estimate)
• Vapor Pressure: 6.69E-17mmHg at 25°C
• Refractive Index: -69 ° (C=1, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.28±0.29(Predicted)
• BRN: 3657855
• CAS DataBase Reference: (-)-Taddol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Taddol(93379-48-7)
• EPA Substance Registry System: (-)-Taddol(93379-48-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/38-36/37/38-20/21/22
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 93379-48-7(Hazardous Substances Data)

Usage

Description

(-)-Taddol, also known as (-)-2,2',6,6'-tetraaryl-1,1'-biphenols, is a chiral, non-racemic, and C2-symmetric diol compound. It is characterized by its unique structure, which features two phenolic hydroxyl groups and a central biphenyl core. (-)-Taddol has gained significant attention in the field of asymmetric catalysis and organic synthesis due to its ability to form strong hydrogen bonds and its versatile reactivity.

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

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

Downstream Products

• 126525-04-0 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with tripropyl-amine 
• 147700-62-7 (1R,7R)-9,9-dimethyl-2,2,4,6,6-pentaphenyl-3,5,8,10-tetraoxa-4-phosphabicyclo<5.3.0>decane 
• 870460-71-2 2-Methyl-acrylic acid [(4R,5R)-5-(hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methyl ester 
• 171979-19-4 (4R,5R)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethyanol dimethacrylate 
• 582298-51-9 1-((3aR,8aR)-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine-6-yl)pyrrolidine 
• 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 

Relevant articles and documents

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

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.

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.