112137-99-2

Upstream product

• 54680-46-5 norephedrine 
• 67-64-1 acetone 
• 75-31-0 isopropylamine 
• 4541-87-1 cis-1-phenylpropene oxide 
• 75-30-9 2-iodo-propane 
• 60980-85-0 2,2,4-trimethyl-5-phenyl-2,3,4,5-tetrahydroisoxazole 
• 52741-17-0 2-isopropylamino-1-phenyl-propan-1-one; hydrochloride 
• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 492-41-1 (1R,2S)-norephedrine 
• 75-26-3 isopropyl bromide 
• 96228-13-6 (1R,2S)-2-Isopropylideneamino-1-phenyl-propan-1-ol 
• 532429-46-2 2,2,4-trimethyl-5-phenyloxazolidine 
• 120443-82-5 (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 10020-96-9 (R)-Mandelonitrile 

Downstream Products

• 24271-96-3 (1RS,2SR)-2-isopropylamino-1-(4-nitro-phenyl)-propan-1-ol 
• 112081-58-0 3-((2S,3R,4S,5R)-3-Isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl)-propionic acid methyl ester 
• 161860-13-5 (2R,3R,4S,5R)-2-Chloro-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 
• 756411-90-2 (-)-(2S,3R)-cis 1-isopropyl-2-methyl-3-phenylaziridine 
• 756411-91-3 (+)-(2S,3S)-trans-1-isopropyl-2-methyl-3-phenylaziridine 
• 652155-32-3 (1R,2S)-N-isopropyl-N-nitroso-2-amino-1-phenyl-1-propanol 
• 87335-43-1 (1R,2S)-1-phenyl-2-(isopropylmethylamino)propanol 
• 704877-41-8 (+)-(1S,2S)-(2-isopropylamino-1-phenylpropyl)diphenylphosphane 
• 704879-58-3 (-)-(1R,2S)-(2-isopropylamino-1-phenylpropyl)diphenylphosphane 
• 112087-32-8 (R)-3-((2S,3R,4S,5R)-3-Isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl)-2-methyl-propionic acid methyl ester 
• 112087-32-8 (S)-3-((2S,3R,4S,5R)-3-Isopropyl-4-methyl-5-phenyl-oxazolidin-2-yl)-2-methyl-propionic acid methyl ester 
• 161860-15-7 (2R,3R,4S,5R)-2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 2-sulfide 
• 161860-14-6 (2S,3R,4S,5R)-2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3-isopropyl-4-methyl-5-phenyl-[1,3,2]oxazaphospholidine 

Relevant academic research and scientific papers

β-Amino alcohols derived from (1R,2S)-norephedrine and (1S,2S)-pseudonorephedrine as catalysts in the asymmetric addition of diethylzinc to aldehydes

A family of N-alkylnorephedrine and N-alkylpseudonorephedrine derived ligands were prepared and applied in the asymmetric alkylation of benzaldehyde using diethylzinc. The absolute configuration of the addition product was directed primarily by the benzylic position of the Ephedra alkaloid, while the magnitude of the enantiomeric ratio was heavily influenced by the nitrogen substituent. However, sterically demanding substituents at the nitrogen position caused the enantioselectivity to be the same for the two diastereomeric systems. Among the ligands that were prepared, it was determined that the N-cyclooctylpseudonorephedrine derivative 7b yielded the highest enantiomeric ratios (87.5:12.5 to 91.0:9.0) when applied in the catalytic asymmetric addition of diethylzinc to aldehydes.

Salicylaldehyde based oxazolidines as catalysts for the asymmetric addition of diethylzinc to aldehydes

(Chemical Equation Presented) A series of oxazolidines have been prepared by condensation of N-isopropyl norephedrine with a variety of salicylaldehyde derivatives. Despite the stereochemical relationship of (1R,2S)-norephedrine with (1R,2S)-ephedrine, th

Dimethylzinc-mediated, enantioselective synthesis of propargylic amines

A one-pot, enantioselective synthesis of N-aryl propargylic amines, using alkynylation reagents obtained from dimethylzinc and terminal acetylenes in combination with various aldehydes and o-methoxyaniline as starting materials, has been developed. Enanti

Intramolecular Chiral Relay at Stereogenic Nitrogen. Synthesis and Application of A New Chiral Auxiliary Derived from (1R,2S)-Norephedrine and Acetone

(1R,2S)-Norephedrine has been employed in the synthesis of a novel 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one via reductive alkylation with acetone, N-nitrosation, reduction, and cyclization. The oxadiazinone was treated with either propionyl chloride or

Preparation of chiral phosphorus(V) reagents and their uses with borane in the enantioselective reduction of ketones

Chiral pentavalent phosphorus reagents 5-17 were prepared from POCl3 and ephedrine (or the related α-amino alcohols), followed by substitution with nucleophiles of phenylmagnesium bromide, alcohols, amines, diamines and triamines. The substitution reactions occurred in a stereospecific manner with retention of the configuration at the phosphorus center. The structures of these phosphorus(V) reagents were determined by spectral methods and verified by X-ray diffraction in several instances. These phosphorus(V) reagents were used with borane/dimethylsulfide complex in the enantioselective reduction of aromatic, aliphatic and heterocyclic ketones. The phosphorus(V) reagents likely functioned as Lewis bases to react with borane, forming in situ zwitterionic species as the chiral reducing agents. The reactions were generally carried out at 0 °C in tetrahydrofuran solution with a molar ratio of ketone/borane/phosphoramidate = 1:1:0.2 to afford secondary alcohols with modest enantioselectivity, up to 67% ee in the reduction of 4′-methylacetophenone.

Stereoselective synthesis of (1R)- and (1R,2S)-1-aryl-2-alkylamino alcohols from (R)-cyanohydrins

Hydrogenation of (R)-cyanohydrins (R)-1 with LiAlH4 occurs without racemization to give the (R)-2-amino alcohols (R)-3. (1R,2S)-2-Amino alcohols (1R,2S)-4 are obtained with high diastereoselectivity by addition of methyl Grignard to O-silyl protected cyanohydrins (R)-2 and subsequent hydrogenation with NaBH4. The N-alkylated 2-amino alcohols (R)-8 and (1R,2S)-9 can be prepared either by reductive alkylation of the corresponding 2-amino alcohols (R)-3 and (1R,2S)-4, respectively, or by a transimination reaction of the Grignard addition products with primary amines and subsequent hydrogenation with NaBH4. The lower diastereoselectivity of hydrogenation in case of the N-alkylmino compounds in comparison to the N-unsubstituted imines is explained by a weaker chelating effect.

Mapping the stereochemical course of carbonyl phosphonylation via chiral phosphorodiamidites

The asymmetric phosphonylation of aldehydes via chiral phosphorodiamidites has been examined as a function of the steric profile of the chiral auxiliary employed. Comparison of N-Me and N-(i)Pr-(1R,2S)-ephedrine auxiliaries reveals that the latter results in a consistently stronger preference for (S(p),S(C)) product stereochemistry than the former.

Enantioselective Reaction of Diethylzinc with Arenecarbaldehydes in the Presence of Ephedrine Derivatives

The reaction of diethylzinc with a range of arenecarbaldehydes has been catalysed by N-alkyl ephedrines to give 1-arylpropan-1-ols with good to excellent optical yields.The enantioselectivity of the reaction was substantially improved by the use of a 4 molar excess of the organozinc reagent.

Highly enantioselective photodeconjugation of α,β-unsaturated esters. Origin of the chiral discrimination

The photodeconjugation of α-methyl conjugated esters can be highly enantioselective when carried out in CH2Cl2 or hexane in the presence of catalytic amounts of chiral β-amino alcohols. Enantiomeric excesses (ee %) up to 70% are desc

Reductive Alkylation of β-Alkanolamines with Carbonyl Compounds and Sodium Borohydride

A synthesis of secondary alkylalkanolamines from primary alkanolamines in a rapid process in which overalkylation is virtually suppressed is described.The procedure combines the ease of formation of oxazolidines from alkanolamines with aldehydes or ketones in absolute ethanol and the lability of the newly formed C-O bond toward sodium borohydrode.The entire process is carried out in 15-35 min depending on the carbonyl substrate.