Epoxidation Of Allylic Alcohols

The epoxidation of alkenes is an especially important process because of its capacity to introduce useful functionalization that is also capable of establishing stereochemistry at two vicinal carbon atoms. Allylic alcohols provide an excellent

Methods and Reagents for Green Chemistry: An Introduction, Edited by Pietro Tundo, Alvise Perosa, and Fulvio Zecchini

Copyright © 2007 John Wiley & Sons, Inc.

V-OH

Figure 11.1 Epoxidation of allylic alcohols.

o^R3

R2 V-OH

opportunity for reactivity and enantioselectivity through metal coordination to the alcohol oxygen atom.1 This phenomenon is illustrated superbly by the Sharpless oxidation process (Figure 11.1), which utilizes titanium tetraisopropoxide, diethyl tartrate, and tertiarybutylhydroperoxide to deliver high enantioselectivity and high reliability.2

A more recent approach to the epoxidation of allylic alcohols makes use of a vanadium polyoxometallate, together with a sterically demanding chiral tartrate (or TADDOL) -derived hydroperoxide, to give a highly chemoselective, regiose-lective and enantioselective outcome (Figure 11.2).3

Figure 11.2

Epoxidation of allylic alcohols.

Figure 11.2

Epoxidation of allylic alcohols.

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