Abstract
Abstract Foremost amongst the methods available to the synthetic chemist for the preparation of alkenes is the reaction of carbanions a- to phosphorus with carbonyl compounds (the Wittig reaction and its variants; Chapter 2). The essential principles of the Wittig reaction-the stabilization of a carbanion by the phosphorus atom, reaction of this carbanion with a carbonyl compound, and subsequent elimination-can be extended to the use of anions stabilized by other, non-phosphorus heteroatoms (Scheme 3.1). This chapter will consider alkene formation involving carbanions stabilized by trialkylsilyl groups (Peterson olefination), sulfoximines (Johnson methylenation), sulfones (Julia olefination), and boron. These methods can offer useful alternatives to phosphorus-based olefinations, particularly in terms of ease of isolation of the product and, importantly, in the control of alkene stereochemistry.
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