147700-75-2

Upstream product

• 147700-73-0 (4R,5R)-4,5-bis[chloro(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane 
• 108-86-1 bromobenzene 
• 77-76-9 2,2-dimethoxy-propane 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 93379-48-7 (R,R)-TADDOL 
• 147700-74-1 (4S,5S)-4,5-bis(azido-diphenyl-methyl)-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 147700-76-3 (4S,5S)-N4,N5,2,2-tetramethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanamine 
• 1394855-27-6 C₃₈H₃₄N₄O₄ 
• 1394855-28-7 C₃₈H₃₄N₄O₄*ClH 
• 1394855-15-2 C₃₃H₂₈N₂O₄ 
• 1394855-24-3 C₄₀H₃₅F₆N₃O₂S 
• 1394855-26-5 C₃₈H₃₇N₃O₃ 
• 1399830-18-2 (3aS,8aS)-hexahydro-2,2-dimethyl-4,4,8,8-tetraphenyl-6H-1,3-dioxolo[4,5-e][1,3]diazepine-6-thione 
• 1442686-75-0 C₃₃H₃₃N₃O₂ 
• 1442686-76-1 C₃₉H₃₇N₃O₂ 
• 1442686-78-3 C₄₅H₄₁N₃O₂ 
• 1442686-79-4 C₄₀H₃₉N₃O₃ 
• 1442686-80-7 C₄₂H₄₃N₃O₅ 
• 1442686-81-8 C₄₀H₃₉N₃O₂ 
• 1442686-82-9 C₃₉H₃₆ClN₃O₂ 

Relevant academic research and scientific papers

Based on the chiral diamine spiro skeleton chiral phosphorus nitrile catalyst, preparation method and application thereof

The invention provides a chiral phosphazene catalyst based on a spiro framework adopting chiral diamine, a preparation method and an application of the chiral phosphazene catalyst. The catalyst has a structure represented in the general formula: (RX-)3P=NR', chiral groups are introduced through R and R', and the catalyst has a structure with two seven-membered rings in centered connection through phosphorspirol. Optically pure tartaric acid or substituted hexahydrophthalic acid or 1,2-cyclopentanedicarboxylicacid,(1R,2S)-rel- is taken as a raw material, chiral diamine is generated through esterification, a Grignard reaction, an optional chlorination reaction, an azido reaction and a reduction reaction of the raw material, then chiral diamine and phosphorus pentachloride have a spirocyclization reaction to construct a phosphorspirol-centered screw ring, the chiral phosphazene molecular catalyst is obtained under the alkaline condition, and a method for substituting azido for hydroxyl directly has good application and popularization value. The catalyst has the advantages of high catalysis efficiency, good stereoselectivity, mild conditions, economy, environmental protection, simplicity and convenience in operation and the like as well as popularization and application prospects.

A quaternary phosphonium salt compound and its preparation method

The present invention discloses a quaternary phosphonium salt compound and a preparation method thereof. The method uses cheap and readily available L-tartaric acid as the raw material, and conducts carboxyl esterification, hydroxyl protection, Grignard reaction, azide substitution, azide reduction and final reaction with phosphorus pentachloride, so as to obtain the quaternary phosphonium salt compound. The quaternary phosphonium salt compound is a novel Bronsted acid catalyst (a hydrogen bond donor catalyst), and can be used in the catalysis of asymmetric Mannich reaction, Michael reaction and Henry reaction.

Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles

A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.

Development of tartaric acid derived chiral guanidines and their application to catalytic enantioselective α-hydroxylation of β-dicarbonyl compounds

A novel library of chiral guanidines featuring a tartaric acid skeleton was developed from diethyl l-tartrate. These guanidines are easily accessed with tunable steric and electronic properties. The utilities of the guanidines were highlighted by their ability to catalyze the α-hydroxylation of β-ketoesters and β-diketones with remarkable efficiency and excellent enantioselectivity.

Chiral enantiopure bis(thio)ureas derived from TADDOL and their carboxylate complexation capacity

New chiral enantiopure ureas and thioureas with (R,R)-TADDOL backbone were synthesized. Bis-(thio)ureas with C2 symmetry were obtained from TADDOL iso(thio)cyanates and bifunctional amino-(thio)ureas from TADDAMINE, respectively. These were tested for car

Preparation and characterization of new C2- and C 1-symmetric nitrogen, oxygen, phosphorous, and sulfur derivatives and analogs of TADDOL. part II

TADDOL (=α,α,α′,α′-Tetraaryl-1,3- dioxolane-4,5-dimethanol) and the corresponding dichloride are converted to TADDAMINs (=(4S,5S)-2,2,N,N′-tetramethyl-α,α,α′, α′-tetraphenyl-1,3-dioxolan-4,5-dimethanamines) (Scheme 2) and ureas, 12-15, and to TADDOP derivatives with seven-membered O-P-O ester rings (Schemes 3 and 4). Cl/P-Replacement via the Michaelis-Arbuzov reaction (Scheme 7) on mono- and dichlorides, derived from TADDOL, are described. It was not possible to obtain phosphines with the P-atom attached to the benzhydrylic C-atom of the TADDOL skeleton (Schemes 6 and 7). The X-ray crystal structures (Figs. 1 and 2) of ten of the more than 30 new TADDOL derivatives are discussed. Full experimental details are presented. Copyright

Chiral bis(N-sulfonylamino)phosphine- and TADDOL-phosphite-oxazoline ligands: Synthesis and application in asymmetric catalysis

A series of N,P-ligands has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts for enantioselective allylic alkylation and olefin hydrogenation, respectively.

Preparation of TADDOL derivatives for new applications

(equation presented) TADDOL Substitution of one or both TADDOL OH groups by other functional groups X, Y is key to new applications of this cheap chiral auxiliary. The Appel reaction and treatment with SOCl2 provide the mono-and dichlorides, respectively. The chlorides are, in turn, replaced by various nucleophiles, and further modifications give a large variety of derivatives, including mono-and ditritylated dioxolanes. The new compounds -available in either enantiomeric form - are ready to be used in enantioselective synthesis and as dopants in liquid crystals.

TADDOLs on their way to late transition metal complexes - synthesis and crystal structure of N- and S-containing TADDOL-derived compounds

As a part of our research program aimed at the synthesis of TADDOL-derived ligands with heteroatoms other than oxygen as chelating units, we describe here new or improved routes to amino TADDOL-analogs (4, 5, 17-19, 21, 22, 26, 34 and 35) and thio-TADDOL-analogs (27-30 and 32).The sulfinato-thiolato Pt-complex 44 was prepared by an oxidative insertion of Pt into the S-S-bond of the corresponding thiosulfinate 29.Furthermore, the X-ray crystal structures of some of the new compounds (2-5, 28, 29, 32, 42 and 44) are presented and discussed. - Keywords: TADDOL derivative; chiral ligand; X-ray structure; platinum complex

Derivatives of α,α,α′,α′-Tetraaryl-2,2-dimethyl-1,3- Dioxolan-4,5-Dimethanol (TADDOL) containing nitrogen, sulfur, and phosphorus atoms. New ligands and auxiliaries for enantioselective reactions

α,α,α′,α′-Tetraaryl-2,2-dimethyl-l,3 - dioxolan-4,5-dimethanols are converted to bicyclic phosphites and phosphonites (2a-2e) by reaction with Cl2PR and Cl2POR derivatives. - One or both OH groups of the parent TADDOL can be replaced by Cl (→, 4a, 5a), and the halide in turn substituted by azide (→ 4b, 5b), thiocyanide (→ 6), or sulfide (→ 8). Reduction of the azido group(s) to NH2 and N-alkylation or acylation furnishes a variety of amino alcohols (4c-4f) and diamines (5c-5f), as well as a bis(trifluoroacetamide) (5g). Cyclization of the aminoalcohol (4c) produces a bicyclic system (7), containing a pyrrolidine ring (structure determination by X-ray diffraction). - The new chiral compounds containing nitrogen and phosphorus atoms might be useful ligands and auxiliaries for enantioselective syntheses.