193476-02-7

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1224386-98-4 (2-methoxy-2-oxo-(S)-1-phenylethyl) (R)-α-dibenzylaminophenylacetate 
• 103-49-1 dibenzylamine 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 174023-92-8 D-dibenzylaminophenylglycinal 
• 875-74-1 (R)-phenylglycine 
• 100-46-9 benzylamine 
• 1355025-46-5 (R)-α-(dibenzylamino)phenylacetic acid (S)-1,2-bis(isopropoxycarbonyl)ethyl ester 

Downstream Products

• 174023-92-8 D-dibenzylaminophenylglycinal 
• 249922-64-3 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (R)-2-dibenzylamino-2-phenyl-ethyl ester 
• 180067-82-7 (1R,2R)-1-Dibenzylamino-1-phenyl-butan-2-ol 
• 180067-87-2 (1R,2R)-1-amino-1-phenyl-2-butanol 
• 103-49-1 dibenzylamine 
• 249923-04-4 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2R)-2-dibenzylamino-1-methyl-2-phenyl-ethyl ester 
• 249923-18-0 (1R,2S)-1-Dibenzylamino-1-phenyl-propan-2-ol 
• 267884-82-2 (1S,4S)-N,N-(dibenzyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 267884-77-5 (1S,R,4S)-N,N-(dibenzyl)-4-amino-1-(3,4-dichlorophenyl)-4-phenyl-1-butanol 
• 267884-84-4 cis-(1S,4S)-N-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 267884-85-5 cis-(1S,4S)-N-(tert-butoxycarbonyl)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine 
• 267884-79-7 (4S)-ethyl-4-N,N-(dibenzyl)-4-amino-4-phenyl-(E)-2-butenoate 

Relevant academic research and scientific papers

Iridium-catalyzed asymmetric allylic substitutions with bulky amines/oxidative double bond cleavage - Entry into the reetz synthesis of amino alcohols

Branched allylic amines were prepared by Ir-catalyzed enantioselective allylic aminations with the bulky N-nucleophiles HN(Boc)2 and HNBn2. The products were transformed into N-protected amino aldehydes, which were either reduced or coupled diastereoselectively with organometallic compounds to give vicinal amino alcohols. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application. Ir-catalyzed enantioselective allylic aminations with bulky N-nucleophiles HN(Boc)2 and HNBn2 gave N-protected allylic amines, which were transformed into N-protected chiral amino aldehydes. These are useful chiral building blocks as previously demonstrated by Reetz et al. A formal synthesis of the neurokinin receptor antagonist (+)-L-733060 was carried out as an application.

Stereoselective and regioselective intramolecular Friedel-Crafts reaction of aziridinium ions for synthesis of 4-substituted tetrahydroisoquinolines

Optically active 4-substituted tetrahydroisoquinolines were synthesized via intramolecular Friedel-Crafts (FC) reactions of aziridinium ions in a highly regio- and stereoselective manner. Control experiments suggest the formation and ring-opening of aziri

DAST mediated preparation of β-fluoro-α-aminophosphonates

Herein, we report a new and convenient method for the synthesis of β-fluoro-α-aminophosphonates starting from naturally occurring l-amino acids. A key step in the synthetic protocol involves nucleophilic fluorination of N,N-dibenzylated-β-amino alcohols with diethylaminosulfur trifluoride (DAST).

Dynamic kinetic resolution of (S)-mandelate-derived a-bromo esters in nucleophilic substitution and asymmetric syntheses of 3-substituted morpholin-2-ones

Dynamic kinetic resolution of (S)-mandelate-derived α-bromo esters in nucleophilic substitution reaction has been investigated. Substitutions with various alkyl amine nucleophiles in the presence of TBAI and DIEA can provide various α-amino esters up to 81% yield and 97:3 dr. Also, the substitution of α-bromo esters with N-substituted 2-aminoethanol nucleophiles and following spontaneous cyclization provides a practical protocol for asymmetric syntheses of 3-substituted morpholin-2-ones up to 95:5 er. ARKAT USA, Inc.

Highly enantioselective synthesis of β-amino alcohols: A catalytic version

(Chemical Equation Presented) Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of trifluoroacetic anhydride.

Stereospecific rearrangement of β-amino alcohols catalyzed by H 2SO4

Highly enantioselective rearrangement of β-amino alcohols was realized by using a catalytic amount of H2SO4. Georg Thieme Verlag Stuttgart.

Highly enantioselective synthesis of β-amino alcohols

N,N-Dialkyl-β-amino alcohols derived from α-amino acids can be rearranged enantiospecifically by using TFAA/Et3N/NaOH to give 1,2-amino alcohols with enantiomeric excess up to 99%.

An expedient total synthesis of cis-(+)-sertraline from D-phenylglycine

An efficient and practical total synthesis of cis-(+)-Sertraline is developed involving intramolecular Friedel-Crafts cyclization of an appropriately tailored D-phenylglycine. (C) 2000 Elsevier Science Ltd.