Regioselective hydroxylations of 1,3-dienes via hydrocobaltation reactions. Facile conversion of myrcene to geraniol and to (±)-linalool

Abstract

Regioselective (1,4-) hydrocobaltation of myrcene (1) leads to a 2 : 1 mixture of (E)- and (Z)-allylcobaloximes (2) which can be converted via the corresponding hydroxylamines (5) to geraniol (6a) and nerol (6b); by contrast, in the presence of molecular oxygen, (2) is converted into the peroxyallylcobalt complex (7), a precursor to linalool (8) and to linalool oxide (10).