55441-99-1

Upstream product

• 124414-35-3 2,2'-Bis-methanesulfinyl-[1,1']binaphthalenyl 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 124414-32-0 2-Methanesulfinyl-2'-methylsulfanyl-[1,1']binaphthalenyl 
• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 147923-23-7 <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) 
• 188-57-8 Dinaphtho<2,1-c:1',2'-e><1,2>dithiane 
• 124414-29-5 Dinaphtho<2,1-d:1',2'-g><1,4>dithiocane 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio) 
• 124414-33-1 Dinaphtho<2,1-d:1',2'-f><1,4>dithiocane S-oxide 
• 188-57-8 Dinaphtho<2,1-c:1',2'-e><1,2>dithiane 

Downstream Products

• 122361-59-5 (Ra)-1,1'-binaphthyl-2,2'-disulfonic acid 

Relevant academic research and scientific papers

A Chiral, Dendralenic C-H Acid

We report the synthesis of a chiral dendralenic C H acid, which contains three unsubstituted binaphthyl moieties. This motif and an achiral variant can be made from their corresponding bis(sulfone) precursors in one step. Despite the presence of the enantiopure binaphthyl backbone, the newly designed chiral C H acid showed only poor enantioselectivity in a Mukaiyama aldol reaction. First attempts toward the synthesis of 3,3'-hexasubstituted binaphthyl-based dendralenic acids are also reported.

In situ reaction monitoring reveals a diastereoselective ligand exchange reaction between the intrinsically chiral Au38(SR)24 and chiral thiols

The ligand exchange reaction between racemic Au38(2-PET) 24 (2-PET = 2-phenylethylthiolate) clusters and enantiopure 1,1′-binaphthyl-2,2′-dithiol (BINAS) was monitored in situ using a chiral high-performance liquid chromatography app

PROCESS FOR PRODUCTION OF DISULFONIC ACID COMPOUND, ASYMMETRIC MANNICH CATALYST, PROCESS FOR PRODUCTION OF -AMINOCARBONYL DERIVATIVE, AND NOVEL DISULFONATE SALT

Hexamethylphosphoramide (HMPA) was added to a reaction vessel containing (R)-1,1'-binaphthyl-2,2'-dithiol and potassium hydroxide. The vessel was purged with oxygen and stirred at 80°C for 5 days under 7 atmospheres of oxygen. After being cooled to room temperature, the reaction product was purified to yield potassium (R)-1,1'-binaphthyl-2,2'-disulfonate. The (R)-1,1'-binaphthyl-2,2'-disulfonic acid obtained from the disulfonate and 2,6-diphenylpyridine were stirred in acetonitrile, and then the solvent was evaporated under reduced pressure. Subsequently, magnesium sulfate and distilled CH2Cl2 were added to the reaction product, and the mixture was stirred at room temperature for 30 minutes. The resulting solution was cooled to 0°C. Benzaldehyde imine whose nitrogen is protected with Cbz and subsequently acetyl acetone were dropped into the solution over a period of 1 hour. The resulting mixture was further stirred at 0°C for 30 minutes. A corresponding β-aminocarbonyl derivative was thus produced with an yield of 91% and an enantiomeric excess of 90% ee.

Synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2, 2′-disulfonic acids

A convenient synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2,2′-disulfonic acids (BINSA, 1) was developed. The key was directed ortho-lithiation of BINSA methyl ester 2 with n-BuLi and subsequent reaction with an electrophile. Electrophiles such as Br2, I2, Me3SiOTf, and i-PrOB(Pin) reacted smoothly with 3,3′-dilithiated BINSA methyl ester, and the corresponding 3,3′-dihalo-, 3,3′-bis(trimethylsilyl)-, and 3,3′-diboryl- BINSA derivatives were obtained in yields of 21-78%. This simple synthetic method is highly attractive since the ability to prepare 3,3′- disubstituted BINOLs in advance can be useful.

Highly practical BINOL-derived acid-base combined salt catalysts for the asymmetric direct mannich-type reaction

The catalytic asymmetric direct Mannich-type reaction between aldimines and 1,3-dicarbonyl compounds is one of the most important carbon-carbon bond-forming reactions in organic chemistry. The resulting Mannich adducts can be efficiently transformed into pharmaceutically useful, optically active -amino ketones, -amino esters, -lactams, etc. In the course of our study of chiral acid-base combined salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1-binaphthyl-2,2-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction 2 1,1-Binaphthyl-2,2-disulfonic Acid (BINSA)-Pyridinium Salts 3 Lithium(I) Binaphtholate Salts 4 Magnesium(II) Binaphtholate Salts 5 Calcium(II) Phosphate Salts and Chiral Phosphoric Acids 6 Conclusions. Georg Thieme Verlag Stuttgart · New York.

Pyridinium 1,1′-binaphthyl-2,2′-disulfonates as highly effective chiral Br?nsted acid-base combined salt catalysts for enantioselective mannich-type reaction

We have established, for the first time, a practical synthesis of chiral 1,1′-binaphthyl-2,2′-disulfonic acid (BINSA 1) from inexpensive BINOL. An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using chiral 1?achiral 2,6-diarylpyridine (2) combined salts, which acted as convenient chiral tailor-made Br?nsted acid?base organocatalysts in situ. Copyright

Enantioselective oxidation of thioethers. A route to the resolution of -2,2'-dithiol

A route to the resolution of racemic -2,2'-dithiol 2 is described, involving the transformation of 2 into a series of dithioethers.The latter are subjected to asymmetric oxidation to monosulfoxides by a procedure developed in our laboratory.For some of the thioethers examined the oxidation is highly diastereo- and/or enantioselective.The resolved 2 is then obtained from the optically pure monosulfoxides either by oxidation to the bis-sulfoxides followed by a Pummerer reaction or by a deoxygenation to the dithioether and subsequent reduction.In both cases enantiomerically pure 2 (e.e. > 98percent) was obtained.Keywords: enantioselective oxidation / optical resolution / thioethers / -2,2'-dithiol

ASYMMETRIC OXIDATION OF THIOETHERS. OPTICAL RESOLUTION OF -2,2'-DITHIOL

Almost optically pure (e.e.>98percent) -2,2'-dithiol (2) is obtained by resolution of racemic 2 via the transformation of the sulfidryl functions into the corresponding thioethers 3 which are asymmetrically oxidized to diastereomeric chiral monosulfoxides 4 and then reconverted into 2.The diastereo and enantioselectivity is dependent on the structure of the thioether; i.e. the dimethylthioether 3a gives two diastereomeric sulfoxides 4a in ca. 1:1 ratio, each of them in >98percent e.e., while cyclic dithioethers 3b-d afford a single diastereomeric sulfoxide 4b-d in 46-78percent e.e..