Synthetic Methods Based on Sulfonimides I. S_N2 Displacement of Ditosylamine

Abstract

In organic synthesis oxygen-functionalized carbon compounds (in various oxidation states) are by far the most common intermediates due to their versatility in carbon-carbon bond formation. However in the synthesis of complicated polyfunctional compounds the use of exclusively oxygen-containing functional groups necessitates elaborate schemes of protection and differentiation among these functional groups. Recent syntheses of prostaglandin E₁ ¹ and jasmone² illustrate the use of nitrogen functions (nitrile, amide, amine, nitro groups) as oxygen equivalents. These successes suggest that additional methods for replacing C-N bonds with C-O should be sought