Expedient Synthesis of α-Substituted α, β- Unsaturated γ-Amino Acids (Dipeptide Mimetics); Wittig Reaction of α-Amino Aldehydes with α- Substituted Alkoxycarbonyl Phosphoranes
- 1 April 1999
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 29 (7) , 1143-1155
- https://doi.org/10.1080/00397919908086084
Abstract
Reacting ethoxycarbonyl triphenyl phosphorane with activated alkylhalides in chloroform gave the ylides 4 -12. They react smoothly and in general without racemisation with oc-amino aldehydes resulting in the dipeptide mimetics 15 - 25. Exceptions are the highly labile aldehydes pyridinoalaninal and serinal. Enantiospecificity is proven via enantioselective chromatography.Keywords
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