127927-56-4

Upstream product

• 75-11-6 diiodomethane 
• 15681-48-8 dimethyllithium cuprate 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 220926-32-9 Me₃SiCH₂ZnEt 
• 131150-35-1 (S)-2-(dibenzylamino)-N'-methoxy-N'-methyl-3-phenylpropane amide 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 
• 100-39-0 benzyl bromide 
• 3182-95-4 L-Phenylalaninol 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 917-54-4 methyllithium 
• 127943-39-9 (1R)-[1'(S)-(dibenzylamino)-2'-phenylethyl]oxirane 
• 127927-43-9 Dibenzyl-((S)-1-oxiranyl-2-phenyl-ethyl)-amine 
• 557-20-0 diethylzinc 
• 131150-39-5 (S)-2-(dibenzylamino)-1-phenylpentan-3-one 

Downstream Products

• 114745-02-7 (2S,3S)-2-amino-1-phenyl-3-pentanol 
• 114744-97-7 (4S,5S)-4-Benzyl-5-ethyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Vanadium-catalyzed asymmetric oxidation of sulfides using Schiff base ligands derived from ss-amino alcohols with two stereogenic centers

Novel Schiff base ligands derived from ss-amino alcohols with two stereogenic centers were prepared and. used in the preparation of optically pure sulfoxides by using aqueous hydrogen peroxide as the oxidant. A variety of sulfides were smoothly converted into the corresponding sulfoxides cata-lyzed by the chiral vanadium-Schiff base complex. Good yields (>80%) with excellent: enantioselectivities (>99%ee) were obtained in most cases.

Synthesis of enantiopure (αS,βS)- or (αR,βS)-β- amino alcohols by complete regioselective opening of aminoepoxides by organolithium reagents LiAlH4 or LiAlD4

The reaction of chiral (2R,1′S)- or (2S,1′S)-2-(1-aminoalkyl) epoxides, 1 or 2 with a variety of organolithium compounds to obtain the corresponding (αS,βS)- or (αR,βS)-β-amino alcohols in enantiopure form is reported. In both cases, the opening of the ox

Studies on the Lewis acid mediated cleavage of α-aminoacetals: Synthesis of novel 1,2-aminoethers, and evidence for α-alkoxy aziridinium ion intermediates

The nucleophilic cleavage of α-amino acetals induced by TMSOTf can be used to prepare a wide range of substituted 1,2-aminoethers. In particular, organometallic reagents, N-heterocycles, and enamines all react efficiently to give products in good yield. In appropriate cases, good levels of stereocontrol are possible, but this is very dependent on the nature of the nucleophile and the substrate, with diethylzinc proving particularly effective across a range of substrates. The degree of stereocontrol can be used to infer the nature of the reactive intermediates involved in the reaction. With diethylzinc, it is most likely that the reaction proceeds by coordination of the nucleophile to the amino group followed by transfer of an ethyl group to an α-oxocarbenium ion. With non-coordinating nucleophiles, the stereochemical outcome can be rationalised in terms of addition to the possible α-alkoxy aziridinium ion intermediates.

Enantioselective synthesis of 1,2-, 1,3- and 1,4- aminoalcohols by the addition of dialkylzincs to 1,2-, 1,3- and 1,4- aminoaldehydes

Chiral 1,3- and 1,4- aminoalcohols were prepared by the addition of functionalized dialkylzincs to 1,3-aliphatic and 1,4-unsaturated aminoaldehydes with good to excellent enantioselectivity. Syn- or anti-1,2- aminoalcohols are stereoselectively obtained by asymmetric addition of dialkylzincs to α-aminoaldehydes depending on the choice of the chiral catalyst. A chelate controlled addition is observed if less than stoichiometric amounts of Ti(Oi-Pr)4 are used.

Iodomethylation of Chiral α-Amino Aldehydes by Means of Samarium/Diiodomethane. Application to the Synthesis of Various Enantiomerically Pure Compounds

Chiral iodohydrins 2 have been obtained from α-amino aldehydes 1 and Sm/CH2I2. Treatment of compound 2 with acetic anhydride, NaH, or AgBF4 affords, with high diastereoselectivity, O-protected 3-(dibenzylamino)-1-iodoalkan-2-ol 3, amino epoxides 4, or azetidinium salts 5, respectively. The synthesis of enantiomerically pure allylamines 6 is also described by metallation of 3 with zinc. The reaction of α-amino aldehydes 1 with Sm/CH2I2 and further treatment with organocuprates affords chiral amino alcohols 7 in a one-pot process.

Synthesis of enantiopure syn-β-amino alcohols. A simple case of chelation-controlled additions of diethylzinc to α-(dibenzylamino) aldehydes

Enantiomerically pure syn-2-amino alcohols 6 are prepared by addition of diethylzinc to chiral α-(dibenzylamino) aldehydes 4. The addition is highly stereoselective, leading to syn-2-(dibenzylamino) alcohols 5 with excellent diastereomeric excesses (76-98%). Debenzylation of 5 by hydrogenolysis on Pearlman's catalyst yields quantitatively the amino alcohols 6.

Aldol Reactions of α-(N,N-Dibenzylamino) Ethyl Ketones

Aldol reactions of the sodium enolates of α-(N,N-dibenzylamino) ethyl ketones proceed in a highly diastereoselective fashion and result in the formation of the all syn adduct.The observed stereoselectivities are most easily understood in the context of an open transition state.

NON-RACEMIZING SYNTHESIS AND STEREOSELECTIVE REDUCTION OF CHIRAL α-AMINO KETONES

α-Amino acids can be doubly benzylated at nitrogen, forming N,N-dibenzyl amino acids which can be converted into α-amino ketones 4 without appreciable racemization.The latter undergo stereoselective reduction with NaBH4 under non-chelation control to form

PROTECTIVE GROUP TUNING IN THE STEREOSELECTIVE CONVERSION OF α-AMINO ALDEHYDES INTO AMINOALKYL EPOXIDES

Sulfonium and arsonium ylides of the type CH2=S(CH3)2 and CH2=As(Ph)3 react with doubly protected α-amino aldehydes 1 derived from amino acids to form aminoalkyl epoxides 3/4, diastereofacial selectivity ranging between 86:14 and >95:5.