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DOI: 10.1039/A804147D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 2485-2500

Cross-metathesis of unsaturated α-amino acid derivatives

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Stefano C. G. Biagini, Susan E. GibsonéThomas and Stephen P. Keen

Abstract

Cross-metathesis of homoallylglycine derivatives with aryl- and alkyl-substituted alkenes using the ruthenium catalyst (Cy3P)2Cl2Ru[double bond, length half m-dash]CHPh 1 has been achieved in 43–55 and 55–66% yield respectively. Allylglycine, vinylglycine and dehydroalanine derivatives have also been examined. Whilst cross-metathesis of allylglycine derivatives with alkyl-substituted alkenes using catalyst 1 may be regarded as a synthetically useful procedure, cross-metathesis reactions of vinylglycine and dehydroalanine derivatives using catalyst 1 are non-viable. Attachment of FmocHagOH 13 to a capped Wang resin, cross-metathesis with dodec-1-ene, and product removal from the resin gives the cross-metathesis product in 74% yield based on FmocHagOH.

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