Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant.

Jayasree Seayad, Abdul Majeed Seayad, Christina L L Chai

Institute of Chemical and Engineering Sciences, 1 Pesek Road, Singapore 627833. jayasree_seayad@ices.a-star.edu.sg

Organic letters 2010 Apr 2

filter terms:

Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions. The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.

Citation

Jayasree Seayad, Abdul Majeed Seayad, Christina L L Chai. Copper-catalyzed diacetoxylation of olefins using PhI(OAc)2 as oxidant. Organic letters. 2010 Apr 2;12(7):1412-5