118169-12-3

Upstream product

• 1469-70-1 allyl ethyl carbonate 
• 81167-39-7 methyl N-(diphenylmethylene)glycinate 
• 4659-45-4 2,6-Dichlorobenzoyl chloride 
• 106-95-6 allyl bromide 
• 67-56-1 methanol 
• 1013-88-3 Benzophenone imine 
• 4530-20-5 BOC-glycine 
• 173201-94-0 methyl N-(diphenylmethyl)iminoacetate 
• 591-87-7 Allyl acetate 
• 220280-64-8 (4S,5R)-(-)-1-[2'-(diphenylmethyleneamino)acetyl]-3,4-dimethyl-5-phenyl-2-imidazolidinone 
• 220280-69-3 (4S,5R)-1-[(S)-2-(Benzhydrylidene-amino)-pent-4-enoyl]-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 91-00-9 Benzhydrylamine 
• 167904-79-2 methyl (R,S)-2-(N-diphenylmethylidene)aminopent-4-ynoate 

Downstream Products

• 150652-96-3 (R)-2-(tert-butoxycarbonyl)amino-4-pentenoic acid methyl ester 
• 188359-85-5 (R)-tert-butyl (1-hydroxypent-4-en-2-yl)carbamate 
• 115289-55-9 methyl DL-2-amino-4-pentenoate hydrochloride 

Relevant academic research and scientific papers

Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.

Preparation of chiral amino esters by asymmetric phase-transfer catalyzed alkylations of schiff bases in a ball mill

The asymmetric alkylation of Schiff bases under basic conditions in a ball mill was performed. The starting Schiff bases of glycine were prepared beforehand by milling protected glycine hydrochloride and benzophenone imine, in the absence of solvent. The Schiff base was then reacted with a halogenated derivative in a ball mill in the presence of KOH. By adding a chiral ammonium salt derived from cinchonidine, the reaction proceeded asymmetrically under phase-transfer catalysis conditions, giving excellent yields and enantiomeric excesses up to 75 %. Because an equimolar amount of starting material was used, purification was greatly simplified. Copyright

Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain

The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.

A new method for the preparation of functionalized unnatural α-H-α-amino acid derivatives

A new method for the preparation of α-H-α-amino acids is reported based on the α-alkylation of iminoacetic acid esters or amides. These imines are readily available by the reaction of glyoxylic acid esters with branched primary amines. The subsequent reaction with methanolic ammonia gave the corresponding iminoacetic acid amides. α-Alkylation of these imines with various electrophiles under basic conditions, followed by an acidic hydrolysis, gave α-amino acids, esters, or amides in up to 93% yield. α-Alkylation under chiral PTC conditions resulted in mono-alkylated amino acids with 90% ee.

Highly enantioselective alkylation of glycine methyl and ethyl ester derivatives under phase-transfer conditions: Its synthetic advantage

Phase-transfer alkylation of the benzophenone Schiff base of glycine methyl or ethyl ester (2) was found to be catalyzed by 3,4,5-F 3-C6H2-NAS-Br [(S,S)-1] with high efficiency and excellent enantioselectivity. This procedure allows facile derivatization of the resulting alkylation products to other synthetically useful chiral building blocks.

1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids

New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 °C,) conditions; (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 °C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 °C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding α-amino acid, (c) in the presence of DBU in methanol to provide N-protected α-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected α-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-α-amino acids.

Poly(ethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivatives

A Schiff base protected glycine supported on a soluble polymer such as poly(ethylene glycol) reacted readily with various electrophiles in the presence of an inorganic base under microwave activation. It was shown in this study that the polymer support also serves as solvent in these reactions. Various α-aminoacids derivatives could be synthesized using this method. (C) 2000 Elsevier Science Ltd.

Reaction of dihalocarbenes with N-Alkylidene amino acid esters and nitriles. Synthesis of aziridine and pyrrole amino acid derivatives

Conditions for preparation of functionalized geminal dihaloaziridines by reaction of dihalocarbenes with N-benzhydrylidene amino acid esters and nitriles were found. The direction of transformations of the intermediate azomethine ylides depends on the structure of the latter, as deduced from MNDO calculations.

Polyethylene glycol (PEG) as polymeric support and phase-transfer catalyst in the soluble polymer liquid phase synthesis of α-amino esters

α-Substituted α-amino esters were synthesized in liquid-phase by polyethylene glycol (PEG) promoted alkylation of a polyethylene glycol-supported Schiff base activated glycine ester.

Asymmetric induction reactions. VII. Palladium-catalyzed asymmetric α- allylations of carbonyl compounds using chiral sulfonamides as chiral ligands

Palladium-catalyzed asymmetric α-allylations of carbonyl compounds were studied using various kinds of chiral sulfonamides derived from optically active α-amino acids as chiral ligands. Participation of the sulfonamide functionality in the palladium catalysis is discussed.