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27.1.3.2.1 Method 1: Reaction of Sulfonium Ylides with Aldehydes and Ketones

DOI: 10.1055/sos-SD-027-00002

Aggarwal, V.; Richardson, J.Science of Synthesis, (20042770.

In 1958, Johnson and LaCount reported the first example of the reaction of a sulfur ylide with an aldehyde to give an epoxide.[‌12‌] In a seminal work four years later,[‌230‌] Corey and Chaykovsky reported the general application of sulfonium ylide 101 with a wide range carbonyl compounds to give epoxides 133 (Scheme 70); this additionelimination reaction has become known as the CoreyChaykovsky reaction and is clearly analogous to the epoxidation of carbonyl compounds using sulfoxonium ylides (see Section 27.1.2.2.1). The epoxidation of carbonyl compounds in this way is one of the most common applications of such species in organic synthesis. The epoxidation of such carbonyl species with sulfonium ylides represents a complimentary method to the Wittig alkenation followed by alkene oxidation that might otherwise be employed to achieve the same overall transformation.

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