TUNABLE STEREOSELECTIVITY IN THE ADDITION OF 2-LITHIOTHIAZOLE TO L-SERINAL DERIVED N-BENZYL NITRONE - SYNTHESIS OF C-2 EPIMER 2,3-DIAMINO-4-HYDROXYBUTANALS

A complete reversal of diastereoselectivity (ds greater than or equal to 95%) in the addition of 2-lithiothiazole to L-serinal derived N-benzyl nitrone has been achieved by the change of the hydroxy and amino protective groups in the aldehyde moiety; the resultant epimeric 2-thiazolyl N-benzyl hydroxylamines were converted to C-2 epimer 2,3-diamino-4-hydroxybutanals via reductive dehydroxylation and thiazolyl-to-formyl conversion.