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- W2953128839 abstract "Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean SN2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities." @default.
- W2953128839 created "2019-06-27" @default.
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- W2953128839 date "1995-01-01" @default.
- W2953128839 modified "2023-09-23" @default.
- W2953128839 title "Synthesis of Optically Active β,γ-Unsaturated α-Amino Acids and of α,β-Unsaturated γ-Amino Acids. SN2- vs. SN2’-Dichotomy of the Mitsunobu Amination of Allylic Alcohols" @default.
- W2953128839 doi "https://doi.org/10.1055/s-1995-3847" @default.
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