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Issue 3, 2001
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Stereocontrolled synthesis of (2S *,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement

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Abstract

The first racemic synthesis of the non-proteinogenic amino acid (2S,3R,4R)-4-hydroxy-3-methylproline (1) has been achieved via iodolactonisation of an unnatural amino acid derivative 4. The relative stereochemistry was derived from an efficient silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement of 2.

Graphical abstract: Stereocontrolled synthesis of (2S [ ] *,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement

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Publication details

The article was received on 19 Sep 2000, accepted on 20 Dec 2000 and first published on 16 Jan 2001


Article type: Paper
DOI: 10.1039/B007586H
Citation: J. Chem. Soc., Perkin Trans. 1, 2001, 267-269
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    Stereocontrolled synthesis of (2S *,3R*,4R*)-4-hydroxy-3-methylproline using a silicon assisted aza-[2,3]-Wittig sigmatropic rearrangement

    J. C. Anderson and A. Flaherty, J. Chem. Soc., Perkin Trans. 1, 2001, 267
    DOI: 10.1039/B007586H

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