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Issue 26, 2018
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Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

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Abstract

A base-induced dearomative [2,3] sigmatropic rearrangement of amino acid ester-derived ammonium salts followed by 1,4-elimination produced α-(ortho-vinylphenyl)amino acid esters. The reaction of azetidine-2-carboxylic acid-derived ammonium salt, (1S,2S,1′R)-3b, proceeded with a perfect N-to-C chirality transfer to afford α-(ortho-vinylphenyl)azetidine-2-carboxylic acid ester, (R)-5 (99% ee). On the other hand, the reaction of glycine-derived ammonium salt (R)-6a, which involves an efficient chirality transfer from a chiral benzylic carbon to an α-carbon of an ester carbonyl giving the optically active α-(ortho-vinylphenyl)glycine ester, (R)-8a (85% ee), was demonstrated. Although this dearomative [2,3] rearrangement followed by 1,4-elimination has limitations with regard to the structures of the substrates, our method provides unique access to substituted α-arylamino acid derivatives.

Graphical abstract: Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

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Publication details

The article was received on 10 May 2018, accepted on 13 Jun 2018 and first published on 13 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01091A
Citation: Org. Biomol. Chem., 2018,16, 4833-4839
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    Dearomative [2,3] sigmatropic rearrangement of ammonium ylides followed by 1,4-elimination to form α-(ortho-vinylphenyl)amino acid esters

    E. Tayama and S. Sotome, Org. Biomol. Chem., 2018, 16, 4833
    DOI: 10.1039/C8OB01091A

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