An optimised and recoverable tartrate surrogate for sharpless asymmetric epoxidations

The tetrahydroxy diester 7d (R = iPr) is almost as effective as diisopropyl tartrate in SAE reactions of (E)-allylic alcohols and can be recovered and re-used following a relatively simple work-up procedure.

The readily synthesised tetrahydroxy diester A is shown to be almost as effective as tartrate esters in the Sharpless asymmetric epoxidations [SAE] of allylic alcohols, and is also amenable to recovery and reuse, following a relatively simple solvent extraction procedure.