127927-55-3

Upstream product

• 15681-48-8 lithium dimethylcuprate 
• 127927-43-9 Dibenzyl-((S)-1-oxiranyl-2-phenyl-ethyl)-amine 
• 925-90-6 ethylmagnesium bromide 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 557-20-0 diethylzinc 
• 75-11-6 diiodomethane 
• 15681-48-8 dimethyllithium cuprate 
• 220926-32-9 Me₃SiCH₂ZnEt 
• 100-39-0 benzyl bromide 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 131150-35-1 (S)-2-(dibenzylamino)-N'-methoxy-N'-methyl-3-phenylpropane amide 
• 95437-43-7 (S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 180187-02-4 (2S,3R)-2-amino-1-phenylpentan-3-ol 
• 114745-01-6 (4S,5R)-4-Benzyl-5-ethyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Direct stereoselective synthesis of enantiomerically pure anti -β-amino alcohols

Enantiomerically pure anti-β-amino alcohols were synthesized from optically pure α-(N,N-dibenzylamino)benzyl esters, derived from α-amino acids, by the sequential reduction to aldehyde with DIBAL-H at -78 °C and subsequent in situ addition of Grignard reagents. Besides anti-β-amino alcohols, anti-2-amino-1,3-diols and anti-3-amino-1,4-diols were obtained in good yields (60-95%) and excellent stereoselectivity (de > 95%). Our technique is compatible with free hydroxyl groups present in the substrate. To demonstrate the versatility of the method, spisulosine and sphinganine were synthesized in two steps from the appropriate N,N-dibenzyl-l-aminobenzyl ester in 42% and 45% yield, respectively.

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

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.

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.