127180-88-5

Upstream product

• 875-74-1 (R)-phenylglycine 
• 74-88-4 methyl iodide 
• 56613-80-0 D-2-phenylglycinol 
• 860304-23-0 (R)-2-N,N-diallylamino-2-phenylethanol 
• 860304-24-1 N,N-diallyl-N-[(1R)-2-methoxy-1-phenylethyl]amine 
• 74879-43-9 (R)-N-benzylidene-2-hydroxy-1-phenylethylamine 

Downstream Products

• 104942-87-2 R(-)-N-(1-phenyl-2-methoxyethyl)-N-trimethylsilylmethylamine 
• 144302-38-5 (R)-benzylidene-(2-methoxy-1-phenylethyl)amine 
• 139224-99-0 (S)-((R)-2-Methoxy-1-phenyl-ethylamino)-p-tolyl-acetonitrile 
• 159116-87-7 (R)-2-methoxy-N-(2-methylpropylidene)-1-phenylethylamine 
• 175787-67-4 1-((R)-2-Methoxy-1-phenyl-ethyl)-1,5-dihydro-pyrrol-2-one 
• 159116-89-9 ((R)-2-Methoxy-1-phenyl-ethyl)-[3-methylsulfanyl-prop-(E)-ylidene]-amine 
• 159116-91-3 4-[(E)-(R)-2-Methoxy-1-phenyl-ethylimino]-butyric acid tert-butyl ester 
• 159116-90-2 [2-Benzyloxy-eth-(E)-ylidene]-((R)-2-methoxy-1-phenyl-ethyl)-amine 
• 159116-86-6 [2-Cyclohexyl-eth-(E)-ylidene]-((R)-2-methoxy-1-phenyl-ethyl)-amine 
• 159171-44-5 ((R)-2-Methoxy-1-phenyl-ethyl)-[3-methyl-but-(E)-ylidene]-amine 
• 204974-19-6 (1R,2S)-2-Ethyl-1-((R)-2-methoxy-1-phenyl-ethylamino)-cyclopropanecarbonitrile 
• 204974-20-9 (1S,2R)-2-Ethyl-1-((R)-2-methoxy-1-phenyl-ethylamino)-cyclopropanecarbonitrile 
• 204973-82-0 (1R,2S)-1-((R)-2-Methoxy-1-phenyl-ethylamino)-2-methyl-cyclopropanecarbonitrile 
• 252334-54-6 (R)-(E)-N-Butylidene-2-methoxy-1-phenylethylamine 

Relevant academic research and scientific papers

Origins of stereoselectivity in optically pure phenylethaniminopyridine tris-chelates M(NN′)3n+ (M = Mn, Fe, Co, Ni and Zn)

One-pot reactions of 2-pyridinecarboxaldehyde, chiral phenylethanamines and Fe(ii) give single diastereomer fac diimine complexes at thermodynamic equilibrium so that no chiral separations are required (d.r. > 200:1). The origins of this stereoselectivity are partly steric and partly a result of the presence of three sets of inter-ligand parallel-offset π-stacking interactions. Mn(ii), Co(ii), Co(iii), Ni(ii) and Zn(ii) give similar fac structures, alongside the imidazole analogues for Fe(ii). While most of the complexes are paramagnetic, the series of molecular structures allows us to assess the influence of the π-stacking present, and there is a strong correlation between this and the M-N bond length. Fe(ii) is close to optimal. For the larger Zn(ii) ion, very weak π-stacking leads to poorer measured stereoselectivity (NMR) but this is improved with increased solvent polarity. The mechanism of stereoselection is further investigated via DFT calculations, chiroptical spectroscopy and the use of synthetic probes.

Monofluoroalkene-Isostere as a 19F NMR Label for the Peptide Backbone: Synthesis and Evaluation in Membrane-Bound PGLa and (KIGAKI)3

Solid-state 19F NMR is a powerful method to study the interactions of biologically active peptides with membranes. So far, in labelled peptides, the 19F-reporter group has always been installed on the side chain of an amino acid. Given the fact that monofluoroalkenes are non-hydrolyzable peptide bond mimics, we have synthesized a monofluoroalkene-based dipeptide isostere, Val-Ψ[(Z)-CF=CH]-Gly, and inserted it in the sequence of two well-studied antimicrobial peptides: PGLa and (KIGAKI)3 are representatives of an α-helix and a β-sheet. The conformations and biological activities of these labeled peptides were studied to assess the suitability of monofluoroalkenes for 19F NMR structure analysis.

Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

A base-induced dearomative [2,3] sigmatropic rearrangement of amino acid ester-derived ammonium salts followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters. The reaction of azetidine-2-carboxylic acid-derived ammonium salt, (1S,2S,1′R)-3b, proceeded with a perfect N-to-C chirality transfer to afford α-(ortho-vinylphenyl)azetidine-2-carboxylic acid ester, (R)-5 (99% ee). On the other hand, the reaction of glycine-derived ammonium salt (R)-6a, which involves an efficient chirality transfer from a chiral benzylic carbon to an α-carbon of an ester carbonyl giving the optically active α-(ortho-vinylphenyl)glycine ester, (R)-8a (85% ee), was demonstrated. Although this dearomative [2,3] rearrangement followed by 1,4-elimination has limitations with regard to the structures of the substrates, our method provides unique access to substituted α-arylamino acid derivatives.

A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation

The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction

The chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams was investigated from ethylbromodifluoroacetate and imines during Reformatsky reaction. Influence of various reaction parameters, such as nature of the amine part, nature of the chiral auxiliary, was evaluated. High levels of stereoselectivity (up to 98%) were obtained for gem-difluoro-β-aminoesters and gem-difluoro-β-lactams using either (R)-phenylglycinol or (R)-methoxyphenylglycinol.

Functionalized pyrrolidines inhibit α-mannosidase activity and growth of human glioblastoma and melanoma cells

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases we

Diastereoselective addition of organozinc reagents to chiral α-imino esters

The addition of organozinc reagents to chiral α-imino esters pre-complexed with zinc bromide, occurred with complete regioselectivity at the imino carbon. The influence of the solvent, temperature and different chiral auxiliaries was studied. The best diastereoselectivities were obtained in Et2O or CH2Cl2 at 0°C, using phenylglycinol methyl ether as the chiral inductor.

Asymmetric functionalization of a chiral non-racemic oxazolidine ester enolate. A new route towards the preparation of quaternary serine esters

A new route towards the preparation of enantiomerically pure quaternary serine esters is described. The key step involves the diastereoselective functionalization of an oxazolidine ester enolate having an exocyclic chiral appendage. (C) 2000 Elsevier Science Ltd.

Et3B- and et2Zn-mediated radical additions to glyoxylate imines, compared stereoinductions

1,3-Stereoinduction in the addition of alkyl radicals to glyoxylic imines derived from various chiral amines has been investigated. New synthetic methodologies involving Et3B and Et2Zn as mediators have been compared. Dihydro-1,4-oxazin-2-one (2b) gave the highest d.e. but no chemoselectivity. Open chain analogues derived from β-alkoxyamines led to good stereoinduction when the reaction was performed with Et2Zn which is a bidentate complexing reagent. (C) 2000 Elsevier Science Ltd.