28116-94-1

Upstream product

• 186581-53-3 diazomethane 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 106943-08-2 (S)-1-bromo-4-phenyl-3-phthalimidobutan-2-one 
• 183196-86-3 methyl (S)-4-phenyl-3-phthalimidobutanoate 
• 333359-21-0 Acetic acid (S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-4-phenyl-butyl ester 
• 67865-74-1 N-phthaloyl-(3S)-3-amino-1-chloro-4-phenyl-2-butanone 
• 1304134-13-1 C₁₈H₁₆ClNO₃ 
• 147224-28-0 2-((S)-3-Azido-1-benzyl-2-oxo-propyl)-isoindole-1,3-dione 
• 183196-81-8 (S)-(4-phenyl-3-phthalimidobutanoyl)dimethylphenylsilane 
• 221467-81-8 (6S)-4-(dimethylphenylsilyl)-7-phenyl-6-phthalimido-1-hepten-4-ol 
• 63328-07-4 (S)-4-phenyl-3-phthalimidobutanoic acid 
• 183196-80-7 (S)-4-phenyl-3-phthalimidobutanoyl chloride 
• 240426-49-7 2-((1S,2R)-1-Benzyl-3-bromo-2-hydroxy-propyl)-isoindole-1,3-dione 

Relevant academic research and scientific papers

REDUCTION OF ALDEHYDES AND KETONES TO ALCOHOLS

The embodiments described herein provide a reduction of an aldehyde or a ketone, such as a Meerwein-Ponnorf-Verley (MPV) reaction of an aldehyde or ketone. In some embodiments, the reaction occurs in the presence of A1[OC(CH3)3]. In some embodiments, the reaction occurs in the presence of an aprotic solvent. In some embodiments, the aldehyde or ketone is an amino aldehyde or an amino ketone wherein the amine is group is protected such that the nitrogen of the amine has no proton. Other embodiments related to compositions and compounds related to the reduction reaction, or to the preparation or use of the aldehyde, the ketone, or the resulting alcohol.

Diastereoselective reduction of N-phthaloyl α-amino ketones: Synthesis of syn-3-amino-1,2-diol derivatives

LiAlH(OBu-t)3 reduction of the chiral-pool derived N-phthaloyl α-amino-α′-acetoxy ketones has led to a facile diastereoselective synthesis of syn-3-amino-1,2-diols (> 75% de).

Synthesis of enantiopure β- and γ-amino alcohols from homochiral α- and β-aminoacylsilanes as stable synthetic equivalents of α- and β-amino aldehydes

A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen- protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3- catalyzed anylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.

Newly designed acylsilanes as versatile tools in organic synthesis

Structural variations in acylsilane molecules allow a number of new selective synthetic processes to be performed which lead to sulfur-containing heterocycles, highly functionalized and unsaturated polycarbonyl derivatives, polyenes, and β- and γ-aminoalcohols. The synthesis of these compounds, most of them not easily accessible through conventional routes, takes advantage of the site-selective reactions occurring at the C-Si bonds, of the increased stability of acylsilanes with respect to that of the corresponding aldehydes and of the high diastereofacial selectivity introduced by the SiR3 group. Herein we report the different synthetic strategies leading to the synthesis of several functionalized acylsilanes and their synthetic applications. The use of new selective polymetallic reagents for the nucleophilic silylation will be presented as well.