87783-01-5Relevant academic research and scientific papers
Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis
Morisset, Eléonore,Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me
supporting information, p. 388 - 392 (2020/01/24)
Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.
Synthesis of triphosphorous bidentate phosphine-phosphoramidite ligands: Application in the highly enantioselective hydrogenation of ortho-substituted aryl enamides
Zhang, Weicheng,Zhang, Xumu
, p. 5515 - 5518 (2007/10/03)
New couple: A novel combination of phosphine and phosphoramidite groups is applied to the preparation of pseudo-C2-symmetric triphosphorous bidentate phosphine-phosphoramidite ligands 1. Unprecedented enantioselectivities toward ortho-substituted aryl enamides and a 1-naphthylenamide in Rh-catalyzed hydrogenation reactions are obtained. (Chemical Equation Presented).
Stereoselective Aldol Reaction with Chiral Secondary Acetamides
Devant, Ralf,Braun, Manfred
, p. 2191 - 2207 (2007/10/02)
The deprotonated acetamides 4a - c and 5a - c are added to prochiral carbonyl compounds.The influence of the solvent, of the reaction temperature, and of the enolate gegenion on the ratio of the isomeric products 8/9, 18/19, and 26/27, respectively, are studied.The highest degree of diastereoselectivity are observed, when the titanium enolate of the acetamide 4a or the threefold deprotonated N-acetyl-α-phenylglycinol (5a) is used.The diastereomers 18a - d, formed in excess in the addition of 5a to aldehydes, are isolated in pure from by a single recrystallization, and afford the enantiomerically pure β-hydroxy carboxylic acids 3a - d.Thereby, the chiral auxiliary, α-phenylglycinol (14), is recovered.
A Chiral Recognition Model for the Chromatographic Resolution of N-Acylated 1-Aryl-1-aminoalkanes
Pirkle, William H.,Welch, Christopher J.,Hyun, Myung Ho
, p. 5022 - 5026 (2007/10/02)
The enantiomers of N-acyl derivatives of 1-aryl-1-aminoalkanes generally may be chromatographically separated on a silica-bonded chiral stationary phase derived from N-(3,5-dinitrobenzoyl)phenylglycine.Chiral recognition is enhanced by increases in either the ? basicity of the aryl substituent or the size of the alkyl substituent but is diminished by increases in the size of the acyl group.Carbamate and urea derivatives of these amines are also resolvable.Chiral recognition models are proposed to account for the observed chiral recognition and are used to assign absolute configuration to several acylated amines.
