Conversion of an alkene to an epoxide. Concerted oxygen transfer from a peracid preserves the relative stereochemical information of the alkene.
Transfer of an oxidant oxygen atom to an unsaturated substrate, including controlled formation of an epoxide.
Enantioselective oxygen transfer to an allylic alcohol using a titanium–tartrate complex and a hydroperoxide. With the alkene horizontal and its hydroxymethyl substituent at lower right, L-(+)-tartrate directs delivery from the back face and D-(−)-tartrate from the front face. Rotate a structure in its plane to apply the mnemonic; reflecting it changes its stereochemistry.
In hydroxyl-directed epoxidation, hydrogen bonding between an allylic hydroxyl and the oxidant favors oxygen delivery from a particular alkene face. This influences diastereoselectivity without requiring an unchanged preference under every solvent or protecting-group condition.
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