- Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids
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A variety of enantiomerically enriched β,γ-unsaturated-α-amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free γ-13C-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon.
- Rose, Nicholas G.W,Blaskovich, Mark A,Wong, Alex,Lajoie, Gilles A
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p. 1497 - 1507
(2007/10/03)
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