75158-10-0Relevant articles and documents
Asymmetric strecker reaction with chiral amines: A catalyst-free protocol using acetone cyanohydrin in water
Pori, Matteo,Galletti, Paola,Soldati, Roberto,Giacomini, Daria
, p. 1683 - 1695 (2013/04/10)
The synthesis of a series of new chiral α-aminonitriles was achieved in a diastereoselective Strecker reaction in a one-pot procedure with aldehydes, enantiopure amines, and acetone cyanohydrin in water. Primary and secondary amines derived from L-α-amino acids were used as sources of chirality. The reactions proceeded efficiently without any catalyst at room temperature. The diastereoselectivity of the process, and the configurational stability of new chiral α-aminonitriles were investigated. The identification of labile intermediates by NMR analysis, and a proposed mechanism and a model for the asymmetric induction are reported. The chemical transformation of proline-derived chiral α-amino-nitriles into chiral amino-diacids, aminols, and amides is reported. A series of new chiral α-aminonitriles was obtained in a diastereoselective Strecker reaction. Aldehydes were coupled with enantiopure amines derived from L-proline, L-phenylglycine, L-phenyl alanine, and L-tryptophan, in a one-pot procedure using acetone cyanohydrin in water. Copyright
One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes
Sipos, Szabolcs,Jablonkai, István
experimental part, p. 1844 - 1846 (2009/07/17)
A one-pot Strecker reaction using various alkyl, arylalkyl and arylnitriles is developed. Aldimine alanes were generated in situ from nitriles by the addition of diisobutylaluminium hydride, and were converted into the corresponding imines on reaction wit
Iodine as a novel and efficient reagent for the synthesis of α-aminonitriles by a three-component condensation of carbonyl compounds, amines, and trimethylsilyl cyanide
Royer, Laurel,De, Surya K.,Gibbs, Richard A.
, p. 4595 - 4597 (2007/10/03)
A straightforward and general method has been developed for the synthesis of α-aminonitriles by simply combining aldehydes or ketones, amines, and trimethylsilyl cyanides in the presence of a catalytic amount of molecular iodine at room temperature.
Synthesis of new ferrocenyl aminoalcohols and aminonitriles and catalytic properties of the aminoalcohols in the ethylation of benzaldehyde
Patti, Angela,Nicolosi, Giovanni,Howell, James A. S.,Humphries, Kristina
, p. 4381 - 4394 (2007/10/03)
Chiral ferrocenyl aminoalcohols possessing either OH or NR2 functionality α to the ferrocenyl ring were prepared and exhibit modest enantioselectivities for the addition of diethylzinc to benzaldehyde. Chiral ferrocenyl aminonitriles exhibit a facile inversion process in protonic solvents.
Lithium perchlorate/diethylether catalyzed aminocyanation of aldehydes
Heydari, Akbar,Fatemi, Parinaz,Alizadeh, Abdol-Ali
, p. 3049 - 3050 (2007/10/03)
A simple and efficient one-pot method was developed to give α- aminonitriles from aldehydes + amines + TMSCN in LPDE. Optically active α- aminonitriles were snythesized by using (S)-(-)- or (R) (+) α- methylbenzylamine, (S)-(-) α-methylbenzylamine affords
Thermodynamically Controlled 1,3-Asymmetric Induction in an Acyclic System: Equilibration of α-Amino Nitriles Derived from α-Alkylbenzylamines and Aldehydes
Inaba, Takashi,Fujita, Makoto,Ogura, Katsuyuki
, p. 1274 - 1279 (2007/10/02)
Acyclic α-amino nitriles 1, derived from α-alkylbenzylamines 3 and aldehydes 4 via a Strecker-type reaction, readily epimerize in MeOH at the newly emerged asymmetric center α to the cyano group.The equilibrium diastereomeric ratio :
Molecular Structure of a Chiral 3,5-Bridged Pyridine and the Effect of Structure on Circular Dichroic Spectra
Speelman, Johanna C.,Talma, Auke G.,Kellogg, Richard M.,Meetsma, A.,Boer, J. L. de,et al.
, p. 1055 - 1062 (2007/10/02)
The crystal structure of the 3,5-bridged chiral macrocyclic pyridine (4S,14S)-4,14-di(2-propyl)-6,9,12-trioxa-3,15,19-triazabicycloheneicosa-1(21),17,19-triene-2,5,13,16-tetrone (5a) has been determined by crystallographic means.Each unit cell contains two nonequivalent molecules.In each molecule the amide groups are twisted out-of-plane in a conrotatory fashion righ-handedly with respect to the molecular C2 axis viewed along the line from C4 to N1 of the pyridine ring.This twist allows avoidance of potential interaction between the amide nitrogen bonded protons and that bonded to C4 of the pyridine ring.The macrocyclic framework is inherently dissymmetric as a result of this helical twist.This is reflected in the circular dichroism spectrum of 5a, which has two strongly negative effects in the 200-400-nm region, at 218 nm, -58800 and 273 nm, -45600.Very similar CD effects are found for analogues of 5a with at the chiral atoms at the 4,14-positions, methyl groups (6a), tert-butyl groups (6b), and proline (7).Comparison are also made with compounds (8b) derived (in thought) from 5a by transposition of the macrocyclic bridge from the 3,5- to the 2,6-positions.Compound 8a is analogous to 8b save that it is a benzene rather than a pyridine derivative.Several nonmacrocyclic analogues of 5a have also been examined as well as the thiamide derivative of 5a (compound 9) for which a synthesis has been developed.The longer wavelength CD effect in 5a is assigned to the pyridine n-?* transition and the shorter wavelength effect to ?-?* transitions.Attempts to correlate the absolute signs with a recently postulated model fail.A method for synthesis of the unnatural amino acids, (S)-(+)-2-amino-3,3,-dimethylbutanoic acid (13), in enantiomerically pure form is described as well as an NMR method for the determination of the enantiomeric purity of samples of 13.
