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. Dondoni et al., 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, Journal of the Chemical Society, Chemical Communications, (14), 1994, pp. 1731-1733
A complete reversal of diastereoselectivity (ds greater than or equal
to 95%) in the addition of 2-lithiothiazole to L-serinal derived N-ben
zyl nitrone has been achieved by the change of the hydroxy and amino p
rotective groups in the aldehyde moiety; the resultant epimeric 2-thia
zolyl N-benzyl hydroxylamines were converted to C-2 epimer 2,3-diamino
-4-hydroxybutanals via reductive dehydroxylation and thiazolyl-to-form
yl conversion.