Nucleophilic additions of Grignard reagents to N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (BIGN). Synthesis of (2S,3R) and (2S,3S)-3-phenylisoserine☆

Add time:09/08/2019    Source:sciencedirect.com

A remarkable Lewis acid tuning has been observed in the nucleophilic addition of Grignard reagent to BIGN, the N-benzyl nitrone derived from 1,2-O-isopropylidene-D-glyceraldehyde. The obtained α,β-dialkoxy hydroxyl-amines can serve as starting points for the synthesis of both aminodiols and α-hydroxy-β-amino acids. This synthetic approach is illustrated by the synthesis of the antipode of the C-13 side chain of Taxotere as well as its C-3 epimer.

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