Still-Gennari Olefination and its Applications in Organic Synthesis

The Still-Gennari olefination is a widely applied modification of the Horner-Wadsworth-Emmons reaction, allowing access to Z-olefins by carbonyl group transformation. Its synthetic utility is undoubtedly of great significance for organic chemistry, as can be illustrated by the number of citations of the original report by W. C. Still and C. Gennari which up to date has been cited over 1000 times. In 2008 Nobel prize winner Ei-ichi Negishi indicated the Still-Gennari olefination as one of the crucial methods for tolefin synthesis, complementary to palladium-catalyzed alkenylations. Surprisingly, so far there is no review concerning this popular and valuable transformation. Therefore, we aim to comprehensively systematize achievements in this field and to present the scope of applications of the Still-Gennari olefination along with recent examples in the total synthesis of biologically active compounds. Our review is intended to be of interest for the general chemical community as well as to be a helpful source of information for synthetic organic chemists.