Practical Synthesis of Shi's Diester Fructose Derivative for Catalytic Asymmetric Epoxidation of Alkenes

A practical synthesis of Shi's diester 3 for catalytic asymmetric epoxidations has been developed. The catalyst has
been prepared in multigram quantities from d-fructose in
four steps with a 66% overall yield. Efficiency, cost, and
selectivity aspects of the reagents involved for its preparation have been taken care of during its preparation. The
workup procedures have been simplified to the bare minimum, rendering a very practical preparation method. The
well-known high efficiency of this catalyst 3 in the epoxidation of α,β-unsaturated carbonyl compounds has also
proved to be high in unfunctionalized alkenes.