114744-97-7

Upstream product

• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 114744-93-3 ((S)-1-Benzyl-2-hydroxy-butyl)-carbamic acid benzyl ester 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 127927-56-4 (2S,3S)-2-(N,N-dibenzyl)amino-1-phenyl-3-pentanol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 3182-95-4 L-Phenylalaninol 
• 75-44-5 phosgene 
• 114745-02-7 (2S,3S)-2-amino-1-phenyl-3-pentanol 
• 114744-93-3 ((1S,2R)-1-Benzyl-2-hydroxy-butyl)-carbamic acid benzyl ester 

Downstream Products

• 114745-03-8 ((1S,2S)-1-Benzyl-2-hydroxy-butyl)-carbamic acid benzyl ester 
• 114745-01-6 (4S,5R)-4-Benzyl-5-ethyl-oxazolidin-2-one 
• 114745-02-7 (2S,3S)-2-amino-1-phenyl-3-pentanol 

Relevant academic research and scientific papers

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.

ALUMINUM-MEDIATED ONE-POT CONVERSION OF α-AMINO ACID ESTERS TO THREO 2-AMINO ALCOHOLS WITH HIGH DIASTEREOSELECTIVITY

Reduction of N-Cbz α-amino acid esters with DIBAl-H, followed by treatment with Grignard reagent in a one-pot manner gave the corresponding threo 2-amino alcohols with high diastereoselectivity without racemization. KEYWORDS 2-amino alcohol; α-amino acid ester; DIBAL-H reduction; α-amino aldehyde; chelation controll; diastereoselective synthesis; one-pot synthesis

A NEW FACILE DIASTEREOCONVERSION OF 2-AMINO ALCOHOLS INVOLVING A NOVEL CYCLOCARBAMATION

A new practical method for diastereoconversion of 2-amino alcohols was performed by treatment on N-Cbz- derivatives with trifluoromethanesulfonic anhydride or thionyl chloride, followed by ring cleavage of the resulting oxazolidin-2-ones