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Issue 24, 2002
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Synthesis of α,α-disubstituted unnatural amino acid derivatives using the aza-[2,3]-Wittig sigmatropic rearrangement

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Abstract

Aza-[2,3]-Wittig rearrangement precursors derived from alanine, valine, phenylalanine and phenylglycine were synthesised with diethylamide and methylester anion stabilising groups. In the amide series only the alanine derived precursor rearranged upon deprotonation with KH. In the ester series the alanine, valine and phenylalanine precursors rearranged successfully with KH. The phenylalanine ester precursor gave an unselective rearrangement whereas rearrangement of the alanine and valine ester precursors gave levels and sense of diastereoselectivity in line with our transition state model. The products are chiral α,α-disubstituted-α-amino acid derivatives possessing two adjacent stereocentres and a vinyl silane synthetic handle.

Graphical abstract: Synthesis of α,α-disubstituted unnatural amino acid derivatives using the aza-[2,3]-Wittig sigmatropic rearrangement

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Publication details

The article was received on 25 Jul 2002, accepted on 29 Sep 2002 and first published on 15 Nov 2002


Article type: Paper
DOI: 10.1039/B207295E
Citation: J. Chem. Soc., Perkin Trans. 1, 2002,0, 2871-2879
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    Synthesis of α,α-disubstituted unnatural amino acid derivatives using the aza-[2,3]-Wittig sigmatropic rearrangement

    J. C. Anderson and S. Skerratt, J. Chem. Soc., Perkin Trans. 1, 2002, 0, 2871
    DOI: 10.1039/B207295E

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