Scope and Applications in Organic Synthesis

Regio- and stereoselectivity are important considerations in the epoxidation of more complex olefin substrates. In this context it is important to distinguish between two types of effect those which are attributable to electronic and steric factors inherent in the substrate and those which are derived from a particular property of the reagent. An example of the former is the difference in reactivity of double bonds in nonconjugated dienes due to increasing alkyl substitution, as illustrated with limonene (eq. (13)) [31]. 

The synthetic utility of the oxirane technology was further extended by the development by Sharpless and Katsuki [33, 34] of the titanium(lV) tartrate catalyst for the asymmetric epoxidation of allylic alcohols with TBHP (eq. (16)). 

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