Reactivities Of Chiral Tert-butanesulfinamides

Nitrogen-containing organic compounds are widespread on the earth, and extensively used in pharmaceutics and industry. Most of the compounds have chiral amino groups. Therefore asymmetric synthesis of chiral amines is extremely important. Chiral tert-butanesulfinamide is a new type of organic intermediate developed in recent years. It is also an important chiral reagent for the synthesis of chiral drugs and intermediates.The most common chiral sulfinamides are t-butyl-and p-toluene-sulfinamide. Since developed byEllmann in 1997,, inexpensive and commercialble chiral tert-butyl sulfinamide are increasingly widespread used as a chiral reagent for the synthesis of chiral amines, In addition, their derivatives are used as chiral ligands and organic catalysts for asymmetric catalytic reactions.In this paper, (1) N-mono-and N-di-alkylations of chiral tert-butane-and toluenesulfinamides were developed. (2) synthesis of chiral sulfoximine compounds via one-pot reactions of tert-butanesulfinamide and benzyl alcohols, dibenzyl ether, dibenzyl sulfide; (3) self condensation of sulfinamides.This paper is divided into three parts:The first part is review:1. The synthesis methods of sulfinamide including asymmetric selective oxidation and selective synthesis by chiral auxiliaries; 2. The applications of sulfinamide in asymmetric synthesis. tert-Butanesulfinamide of asymmetric induction reaction includes three processes:1) Synthesis of N-tert-butanesulfinimines; 2) 1,2-addition reaction of N-tert-butylsulfinyl ketimine.3) t-butylsulfinyl as a leaving group:3. applications of chiral tert-butanesulfinamide in drug synthesis.The second part is the research and experimental part, divided into three sections.1. Improved N-alkylation reaction system of sulfinamide and can selectively generate mono-and bis-substituted product, get the best reaction conditions:direct selective N-alkylation of chiral t-butanesulfinamide with alkyl halides in the presence of potassium hydroxide under air and room temperature.2. Air base catalyzed chiral tertiary butyl sulfonamide and benzyl alcohol, dibenzyl ether, benzyl mercaptan one-pot synthesis of chiral tertiary butylimide.This method has the originality, mild conditions, and environment-friendly.3.Sulfinamide self condensation reaction and some features of sulfinamide:Mainly elaborated tert-butyl sulfinamide occurs at a temperature of 100-120℃ homocoupling shrink to a molecule of ammonia to produce double substitution product; Diphenylethylene bromine in the presence of tert-butyl sulfonamide may be reacted with dioxane generate phenyl vinyl dioxane, the above reactions were not reported.The third part is the conclusion and discussion section. Primarily determines the optimized experimental conditions, the experimental results were analyzed for a comprehensive discussion of its universality, limitations.