5.1 Epoxidation of Alkenes

A. Berkessel; H. Engler; T. M. Leuther

Abstract

The Sharpless, Jacobsen/Katsuki, and Shi epoxidations are frequently applied in the asymmetric epoxidation of relatively electron-rich alkenes. The development and application of these “classics” has been reviewed numerous times. This chapter covers recent advances in the field, e.g. with regard to the extension of asymmetric epoxidation catalysis to hitherto problematic substrate classes, such as non-conjugated terminal alkenes, or homo- and bis-homoallylic alcohols. At the same time, hydrogen peroxide continues to receive increasing attention as an environmentally friendly and economically attractive terminal oxidant. Examples of efficient organocatalytic epoxidation processes are summarized as well. For electron-poor alkenes, e.g. those carrying carbonyl, nitrile, or sulfone acceptor groups, quite remarkable progress has recently been made both in metal and organocatalysis, and the chapter also includes details of methods and protocols in this area.

Key words

alkenes - oxidation - oxiranes - epoxidation - catalysts - enantioselectivity - iron catalysis - manganese catalysis - ruthenium catalysis - titanium catalysis - tungsten catalysis - vanadium catalysis - zirconium catalysis - organocatalysis - enzyme catalysis

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