Recent Studies on the Peterson Olefination Reaction

Abstract

(α-Iodoalkyl)trimethylsilanes and (α-chloroalkyl)-(dimethyl)phenylsilanes are convenient reagents for the highly stereoselective synthesis of di- and trisubstituted alkenes via the Peterson olefination reaction. Studies that led to the development of these compounds are reviewed. False leads and final successes are placed in context. 1. Introduction 2. Peterson Olefination with Silacyclopentane Reagents: The Hard Road to a Simple Lesson 3. A Convenient Synthesis of α-Haloalkyl Silanes: Potential Alkene Precursors 4. Studies in Reductive Acylation: The Recurrent Wurtz Coupling Problem 5. The Synthesis of α-Stannylsilanes: At Last a Use for (α-Chloroalkyl)(dimethyl)phenylsilanes 6. Grignard Reagents and Trisubstituted Alkene Synthesis 7. Conclusion