203873-70-5

Upstream product

• 106-95-6 allyl bromide 
• 203873-67-0 (S)-methyl 2-(2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 

Downstream Products

• 203873-71-6 N-allyl-tert-butyloxycarbonyl-L-phenylalaninyl-L-phenylalanine methyl ester 
• 869560-29-2 (S)-2-(Allyl-benzoyl-amino)-3-phenyl-propionic acid methyl ester 
• 73270-67-4 (S)-2-allylamino-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

DBU Catalysed Enantioselective Degradative Rearrangement: a Way to Tetrasubstituted 2-Aryl-2-Amino Esters

Herein we report a catalytic, easily scalable protocol for the enantioselective synthesis of Tetrasubstituted α-aryl-α-amino acid derivatives, using a biphasic system composed by catalytic DBU in DME and aqueous solutions of Na2CO3. Under very mild reaction conditions, without using metal or chiral additives, this heterogeneous system promotes the degradative rearrangement of functionalized N-aryl sulphonyl α-amino esters into the corresponding tetrasubstituted 2-aryl-2-amino esters, with high enantiomeric ratios (up to 97.5:2.5) and good yields (up to 95%). (Figure presented.).

3,5-Bis(n-perfluorooctyl)benzyltriethylammonium bromide (F-TEBA): An efficient, easily recoverable fluorous catalyst for solid-liquid PTC reactions

A readily available 3,5-bis(perfluorooctyl)benzyl bromide and triethylamine were reacted under mild conditions to give 3,5-bis(n-perfluorooctyl) benzyltriethylammonium bromide (F-TEBA), an analogue of the versatile phase-transfer catalyst, benzyltriethyla

Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was

N-monoalkylation of α-amino acid esters under solid-liquid PTC conditions

N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N-(4- Nitrophenylsulfonyl)-α-amino acid methyl esters (p-NBSAA-OMe, 5) were N- alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R2- AA-OMe 7 and p-NBS-N-R2-AA-OMe 8 in excellent yields without any detectable racemization.

Site-specific N-alkylation of peptides on the solid phase

A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin.