131150-63-5

Upstream product

• 131150-45-3 (S)-4-Dibenzylamino-6-methyl-heptan-3-one 
• 75-11-6 diiodomethane 
• 15681-48-8 dimethyllithium cuprate 
• 111060-65-2 (S)-2-(dibenzylamino)-4-methylpentanal 
• 131150-36-2 (S)-2-(dibenzylamino)-N'-methoxy-4,N'-dimethylpentane amide 
• 95084-25-6 (S)-2-dibenzylamino-4-methylpentanoic acid 
• 111060-53-8 (S)-2-(N,N-dibenzylamino)-4-methyl-1-pentanol 
• 100-39-0 benzyl bromide 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 917-54-4 methyllithium 
• 557-20-0 diethylzinc 

Relevant academic research and scientific papers

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

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