Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-α-bisabolol and (-)-8-epi-α-bisabolol

Article abstract of DOI:10.1002/anie.200390250

Vanadium triisopropoxide oxide and an α-amino acid-based hydroxamic acid (e.g. 1) form the catalyst for the asymmetric epoxidation of homoallylic alcohols presented here. 3-Substituted alcohols 2 were epoxidized to the corresponding epoxy alcohols 3 with good ee values. In addition, a concise total synthesis of (-)-αand (-)-8-epi-α-bisabolol was achieved.