Tunable stereoselectivity in the addition of 2-lithiothiazole to L-serinal derived N-benzyl nitroe. Synthesis of C-2 epimer 2,3-diamino-4-hydroxybutanals
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 14,p. 1731-1733
- https://doi.org/10.1039/c39940001731
Abstract
A Complete reversal of distereoselectivity (ds 95%) in the addiition of 2-lithiothiazole to L-serinal derived N-benzylnitrone has been achieved by the change of the hydroxy and amino protective gruops in the aldehyde moiety; the resultant epimeric 2-thiazolyl N-benzyl hydroxylamines were converted to C-2 epimer 2,3-diaminio-4-hydroxybutanals via reductive dehydroxylation and thiazolyl-to-formaly conversion.Keywords
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