221468-33-3

Upstream product

• 82495-70-3 (2S)-2-p-toluenesulfonamido-3-phenylpropanol 
• 412908-98-6 (S)-3-[(4-methylphenyl)sulfonyl]-4-phenylmethyl-2-oxazolidinone 
• 98-59-9 p-toluenesulfonyl chloride 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 221467-91-0 (6S)-4--7-phenyl-6-tosylamido-1-hepten-4-ol 
• 221467-77-2 (S)-(4-phenyl-3-tosylamidobutanoyl)dimethylphenylsilane 
• 221468-44-6 (S)-4-phenyl-3-tosylamidobutanoyl chloride 
• 172534-72-4 (3S)-(p-toluenesulfonyl)amino-4-phenylbutyric acid 

Relevant academic research and scientific papers

Decarboxylative isomerization of N-Acyl-2-oxazolidinones to 2-oxazolines

(Chemical Equation Presented) N-Acyl-2-oxazolidinones are ring-opened by lithium iodide and decarboxylated in the presence of a mild proton source. Further reaction with an amine base provides 2-oxazolines. The transformation is general for oxazolidinones unsubstituted in the 5 position and occurs under mild conditions (25-50°C). These results complement the existing methods for this transformation by allowing lower temperatures and/or avoiding metal catalysts.

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.