A mild and efficient method for the stereoselective formation of C-O bonds: palladium-catalyzed allylic etherification using zinc(II) alkoxides

Hahn Kim; Chulbom Lee

doi:10.1021/ol027104u

A mild and efficient method for the stereoselective formation of C-O bonds: palladium-catalyzed allylic etherification using zinc(II) alkoxides

Org Lett. 2002 Nov 28;4(24):4369-71. doi: 10.1021/ol027104u.

Authors

Hahn Kim¹, Chulbom Lee

Affiliation

¹ Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

PMID: 12443100
DOI: 10.1021/ol027104u

Abstract

[reaction: see text] A highly chemo- and stereoselective palladium-catalyzed allylic etherification reaction is described. The use of zinc(II) alkoxides proved effective in promoting the addition of the oxygen nucleophile derived from aliphatic alcohols to eta(3)-allylpalladium complexes. Using diethylzinc (0.5 equiv), 5 mol % of Pd(OAc)(2), and 7.5 mol % of 2-di(tert-butyl)phosphinobiphenyl in THF, the cross-coupling reaction between various aliphatic alcohols and allylic acetates proceeded at ambient temperature to furnish allylic ethers with high stereoselectivity.