𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis and reactivity of enantiomerically pure N-acylN-alkyl p-toluenesulfinamides

✍ Scribed by JoséL. García-Ruano; Raquel Alonso; María M. Zarzuelo; Pedro Noheda

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
555 KB
Volume
6
Category
Article
ISSN
0957-4166

No coin nor oath required. For personal study only.

✦ Synopsis

The syntheses of different enantiomerically N-acyl N-alkyl p-toluenesulfinamides 5, by N-sulfinylation of primary amines with (S)-menthyl-p-tolylsulfinate followed by N-acylation of the resulting sulfinamides are reported. Their reactions with some C-nucleophiles take place at the sulfur atom exclusively with complete retention of the enantiomeric purity, revealing their ability as sulfinylating agents. In this sense, their comparison with other reagents popularly used, revealed that 5 have some important advantages.

📜 SIMILAR VOLUMES

Practical synthesis of N-alkyl-N-glycosy
Practical synthesis of N-alkyl-N-glycosylhydroxylamines, multitalented precursors of enantiomerically pure nitrones
✍ Stefano Cicchi; Massimo Corsi; Marco Marradi; Andrea Goti 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 108 KB

A practical synthesis of N-benzyl-N-glycosylhydroxylamines 3 (R=CH 2 Ph) is reported. The ability of these compounds to act as versatile synthetic intermediates is demonstrated by their oxidation followed by cycloaddition to N-glycosyl isoxazolidines and by the novel direct cycloaddition as masked a