58107-40-7

Upstream product

• 127-65-1 chloroamine-T 
• 110-83-8 cyclohexene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 68820-12-2 cyclohexyl-N-tosyl aziridine 
• 286-20-4 cyclohexene oxide 
• 70-55-3 toluene-4-sulfonamide 
• 676-58-4 methylmagnesium chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 109-89-7 diethylamine 
• 930-68-7 cyclohexenone 
• 58107-40-7 N-(2-hydroxycyclohexyl)-4-methylbenzenesulfonamide 
• 286-20-4 cyclohexane-1,2-epoxide 
• 58107-57-6 4-methyl-N-(2-oxo-cyclohexyl)-benzenesulfonamide 

Downstream Products

• 857003-99-7 1-N-(4-methylphenylsulfonyl)amino-2-O-(4-methylphenylsulfonyl)oxycyclohexane 
• 245085-44-3 (1R,2R)-trans-2-(N-toluene-4-sulfonyl)amino-1-cyclohexanol 
• 69291-77-6 3-(toluene-4-sulfonyl)-octahydro-benzooxazole 
• 58107-40-7 trans-2-(N-tosylamino)-1-cyclohexanol 
• 38898-70-3 cis-2-amino-cyclohexanol-⁽¹⁾ 

Relevant academic research and scientific papers

Cis -1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: OsV(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand

Catalytic activity of [OsIII(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [OsV(O)(NHTs)(L-N4Me2)](PF6)2 (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

Experimental and theoretical investigations of the stereoselective synthesis of P-stereogenic phosphine oxides

An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides has been developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as the chiral auxiliary. The method relies on three key steps: 1) Highly diastereoselective formation of PV oxazaphospholidine, rationalized by a theoretical study; 2) highly diastereoselective ring-opening of the oxazaphospholidine oxide with organometallic reagents that takes place with inversion of configuration at the P atom; 3) enantioselective synthesis of phosphine oxides by cleavage of the remaining P-O bond. Interestingly, the use of a PIII phosphine precursor afforded a P-epimer oxazaphospholidine. Hence, the two enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor, which constitutes a clear advantage for the stereoselective synthesis of sterically hindered phosphine oxides. That's handy: An efficient enantioselective strategy for the synthesis of variously substituted phosphine oxides was developed, incorporating the use of (1S,2S)-2-aminocyclohexanol as a chiral auxiliary, whereby enantiomeric phosphine oxides can be synthesized starting from either a PV or a PIII phosphine precursor.

NaHSO3-Promoted ring openings of n-tosylaziridines and epoxides with H2O

NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired ss-aminoalcohols and ss-diols in good to excellent yields and with uniformly high regioselectivity.

Synthesis of β-fluoro amides using partially hydrated nickel difluoride as fluorine source

P-Fluoro amides were obtained from the reactions of activated aziridines with partially hydrated nickel difluoride (NiF2-nH2O, n 4) in good yields (47-82%) in the presence of tetran-butylammonium fluoride (20 mol%), while the non-ac

Tri-n-butylphosphane catalyzed ring opening of aziridines with secondary amines

Ring opening of aziridine with dialkyl amine took place readily in the presence of catalytic amounts of tri-n-butylphosphane (10 mol%) in the mixture of CH3CN/H2O (10:1), giving corresponding vicinal diamines in mediate to high yield

Diversity-oriented synthesis based on the dppp-catalyzed mixed double-michael reactions of electron-deficient acetylenes and β-amino alcohols

In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)- propane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived β-amino alcohols.

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

Two-step synthesis of N-sulfonyl aziridines from epoxides

A convenient and high-yielding two-step synthesis of N-sulfonyl aziridines starting from epoxides is described. The method, which involves epoxide ring opening with sulfonamides and subsequent mesylation-cyclisation, is particularly suitable for variation

Two-step syntheses of 2,4,6-triisopropylbenzenesulfonyl aziridines

In a continuing study on the α-lithiation of N-tosyl aziridines, it is reported that ortho-lithiation of the N-tosyl group is occurring under typical α-lithiation conditions (s-BuLi/PMDETA). Thus, a simple, two-step synthesis of N-2,4,6-triisopropylbenzen