Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

Abstract

The Wittig olefination utilizing phosphoranes and the related Horner-WadsworthEmmons (HWE) reaction using phosphonates transform aldehydes and ketones into substituted alkenes. Because of the versatility of the reactions and the compatibility of many functional groups towards the transformations, both Wittig olefination and HWE reactions are a mainstay in the arsenal of organic synthesis. Here, an overview is given on Wittig-and Horner-Wadsworth-Emmons (HWE) reactions run in combination with other transformations in one-pot procedures. The focus lies on one-pot oxidation Wittig/HWE protocols, Wittig/HWE olefinations run in concert with metal catalyzed cross-coupling reactions, Domino Wittig/HWE-cycloaddition and Wittig-Michael transformations.

Tandem Baeyer–Villiger/Wittig/oxa-Michael addition: One-step to 5-substituted γ-lactones

“…[30][31][32][33][34][35][36][37] On the other hand, tandem-and one-pot reactions incorporating Wittig reagents represent a commonly used strategy in organic synthesis to prepare diverse synthetically useful compounds. [38][39] In particular, oxidation processes carried out in the presence of a Wittig reagent turned out to be an efficient solution to the difficulties of handling carbonyl intermediates labile and/or difficult to isolate. [40][41][42][43][44][45][46] Accordingly, the development of new efficient and versatile tandem oxidative procedures is desirable.…”