Expedient synthesis of alpha-substituted alpha,beta-unsaturated gamma-amino acids (dipeptide mimetics); Wittig reaction of alpha-amino aldehydes withalpha-substituted alkoxycarbonyl phosphoranes

Authors
Scholz, D Weber-Roth, S Macoratti, E Francotte, E
Citation
D. Scholz et al., Expedient synthesis of alpha-substituted alpha,beta-unsaturated gamma-amino acids (dipeptide mimetics); Wittig reaction of alpha-amino aldehydes withalpha-substituted alkoxycarbonyl phosphoranes, SYN COMMUN, 29(7), 1999, pp. 1143-1155
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
7
Year of publication
1999
Pages
1143 - 1155
Database
ISI
SICI code
0039-7911(1999)29:7<1143:ESOAAG>2.0.ZU;2-D
Abstract
Reacting ethoxycarbonyl triphenyl phosphorane with activated alkylhalides i n chloroform gave the ylides 4 - 12. They react smoothly and in general wit hout racemisation with alpha-amino aldehydes resulting in the dipeptide mim etics 15 - 25. Exceptions are the highly labile aldehydes pyridinoalaninal and serinal. Enantiospecificity is proven via enantioselective chromatograp hy.