Investigation on the Se-Acylation with N-Acylbenzotriazoles

Abstract

The acylation of Se-nucleophiles with N-acylbenzotriazoles was investigated. Samarium phenylselenolate and benzylselenolate (RSeSmI₂) reacted with N-aroyl and N-alkanoylbenzotriazoles smoothly and afforded the corresponding selenol esters in good yields. Treatment of the RSeSmI₂ with α,β-unsaturated N-acylbenzotriazoles afforded the anticipated α,β-unsaturated selenol esters in moderate yields, due mainly to the side reaction of conjugate addition.

GRAPHICAL ABSTRACT      

Asymmetric Epoxidation of Methyl Gibberellate by the Modified Sharpless Reagent

Asymmetric epoxidation of methyl gibberellate by the modified Sharpless reagent in the various temperature is described. Compound 8 and 9 can be used as the key intermediates for synthesis of the polyhydroxygibberellins.