105370-59-0

Upstream product

• 109-72-8 n-butyllithium 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 122-56-5 tributyl borane 
• 862776-58-7 (S)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 911372-70-8 (R_S)-2-methyl-N-((R)-1-phenylpentyl)propane-2-sulfinamide 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 131154-12-6 4-Methyl-benzenesulfinic acid [1-phenyl-pent-(E)-ylidene]-amide 
• 249920-08-9 2,4-diphenyl-1,3-oxazolidine 
• 321-97-1 (1R,2R)-pseudoephedrine 
• 131154-13-7 4-Methyl-benzenesulfinic acid ((R)-1-phenyl-pentyl)-amide 
• 131214-10-3 (2R,1'R)-2-<(1'-phenylpentyl)amino>-2-phenylethanol 

Downstream Products

• 1106777-28-9 (R)-N-(1-phenylpentyl)benzamide 

Relevant academic research and scientific papers

Asymmetric Addition of Butyllithium to N-Metallo Imines of Benzaldehyde

N-Metallo imines derived from benzaldehyde such as N-aluminium imine, N-boryl imine and N-silyl imine were asymmetrically alkylated with butyllithium in the presence of chiral ligands including (-)-sparteine and proline-derived amino alcohols to give optically active 1-phenylpentyl-1-amine in up to 74percent anantiomeric excess.Polymer-supported chiral ligands were also used for the asymmetric addition.

Enantioselective syntheses of α-phenylalkanamines via intermediate addition of Grignard reagents to chiral hydrazones derived from (R)-(-)-2- aminobutan-1-ol

The hydrazine (R)-(-)-28 was obtained in four steps from 2-aminobutan- 1-ol (R)-(-)-11, and reacted with benzaldehyde to give the hydrazone (R)-(- )-29. Nucleophilic addition of various alkyl Grignard reagents to the latter yielded the corresponding trisubstituted hydrazines (R,R)-30a-g in 70-89% yields and having d.e.s=100% (1H and 13C NMR). Catalytic hydrogenolysis of these hydrazines afforded the corresponding (R)(+)-α-phenylalkanamines (R)- (+)-31a-g having e.e.s=90-92% (chiral GPC).

Addition of Highly Polarized Organometallic Compounds to N-tert-Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest

Highly polarized organometallic compounds of s-block elements are added smoothly to chiral N-tert-butanesulfinyl imines in the biodegradable d-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines after quantitatively removing the sulfinyl group. The practicality of the method is further highlighted by proceeding at ambient temperature and under air, with very short reaction times (2 min), enabling the preparation of diastereoisomeric sulfinamides in very good yields (74–98 %) and with a broad substrate scope, and the possibility of scaling up the process. The method is demonstrated in the asymmetric syntheses of both the chiral amine side-chain of (R,R)-Formoterol (96 % ee) and the pharmaceutically relevant (R)-Cinacalcet (98 % ee).

Catalytic asymmetric synthesis of β-sultams as precursors for taurine derivatives

β-Sultams, biologically interesting sulfonyl analogues of β-lactams, have been prepared by an organocata-lytic asymmetric formal [2+ 2]-cycloaddition approach of non-nucleophilic imines with alkyl sulfonyl chlorides. In the case of very electron poor N-to

Studies on the bisoxazoline- and (-)-sparteine-mediated enantioselective addition of organolithium reagents to imines

The enantioselective addition of organolithium reagents to N-anisylaldimines promoted by chiral bisoxazolines and (-)-sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n-Bu, Ph, vinyl) in excellent yields (81-99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.

β-Silylated homopropargylic amines via the asymmetric allenylboration of aldimines

(Chemical Equation Presented) The asymmetric synthesis of α-trimethylsilylpropargylic carbamines (7) through the addition of allenylboranes 4 to N-H aldimines is reported. The insertion of TMSCHN 2 into enantiomerically pure B-alkynyl-10-TMS-9-

Synthesis and applications of chiral organoboranes generated from sulfonium ylides

The reactions of aryl-stabilized sulfonium ylides with trialkyl/triarylboranes have been investigated. Clean monohomologation of the boranes with only a small amount of the higher homologation products (2O2/NaOH) and amines (treatment with NH2OSO3H). Although the reactions were conveniently conducted at 5 °C, the ylide reaction with tributylborane was very fast even at -78 °C (complete after 15 min). Use of chiral sulfides rendered the reactions asymmetric, and high enantioselectivity (>95% ee) was observed in all cases. The ylide-borane reaction was applied to short syntheses of the anti-inflammatory agents neobenodine and cetirizine, both of which contain a chiral diarylmethylalkoxy and diarylmethylamino moiety, respectively. Copyright

Stereoselective Addition Reactions of Chiral N-Benzylidene-p-toluenesulfinamides. Asymmetric Syntheses of β- and γ-Amino Acids

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitril with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate.Treatment of 2 with allylmagnesium bromide in ether at 0 deg C gave the adducts (R)-7 with excellent stereoselectivity.Pure chiral sulfinamides 7 were converted into β- and γ-amino acids in four and five steps, respectively.