84028-95-5

Upstream product

• 84028-88-6 ethyl (S)-lactate triflate 
• 100-46-9 benzylamine 
• 63696-99-1 (S)-ethyl 2-(methylsulfonyloxy)propanoate 
• 687-47-8 (S)-Ethyl lactate 
• 6111-99-5 ethyl diazoalaninate 
• 30365-54-9 ethyl (S)-2-bromopropionate 

Downstream Products

• 131335-55-2 (R)-N-benzyl-2-(benzylamino)propanamide 
• 99956-17-9 (R)-1-Benzyl-5-ethoxy-6-methyl-3,6-dihydro-1H-pyrazin-2-one 
• 99940-70-2 (6R)-1-N-benzyl-6-methyl-piperazine-2,5-dione 
• 188823-00-9 (R)-2-[Benzyl-(2-chloro-acetyl)-amino]-propionic acid ethyl ester 

Relevant academic research and scientific papers

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS

Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

Stereoselective synthesis of dipeptides - I

The alkylation of 7 occurs in moderate to good trans stereoselection (d.e.40-98%), while a poorer d.e. (40-98%) is observed for 8. On the contrary, in both substrates the alkylation with CH3I produces a greater amount of the cis isomer (d.e.48%).). Cleavage of the lactims 9(a,e) gives enantiomerically pure dipeptides 14(a,e). The absolute configuration of the introduced stereogenic centres has been assigned on the basis of the 1H-NMR data in connection with the conformational analysis.

CONTROL OF ENANTIOSELECTIVITY IN THE FORMATION OF A MODEL ALANINAMIDE FROM A 2-BROMOPROPANAMIDE

Reactions of (R)- or (S)-2-chloro or -bromopropanamides 1,2 and related compounds with benzylamine in the presence of AlCl3, Ag2O, or a lipase (CCL) in an organic solvent, are described.N,N'-Dibenzylalaninamide 6 of either optical activity is obtained from optically active 2 by proper use of Ag2O.

Amino Acids, 4 - Enantioselective Synthesis of N-Substituted α-Amino Carboxylic Acids from α-Hydroxy Carboxylic Acids

With primary and secondary amines, the (S)-α-(trifluoromethylsulfonyloxy) carboxylates (S)-3 afford in an SN2 reaction the N-substituted (R)-α-amino carboxylates (R)-5, (R)-9, and (R)-12, resp.The rates of α-substituted ethyl propionates decrease in the order of the substituents triflate (3a) >> bromide (8a) > mesylate (7a) >= tosylate (7b) > chloride (8b); in the reactions with amines, decreasing reactivity affords increasing racemisation and elimination as a consequence of the more drastic conditions which are required