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Titolo:
SYNTHESIS AND CRYSTAL-STRUCTURE OF ENANTIOPURE N-TRITYLAZIRIDIN-2-YL-METHANOLS FROM L-SERINE AND L-THREONINE
Autore:
WILLEMS JGH; HERSMIS MC; DEGELDER R; SMITS JMM; HAMMINK JB; DOMMERHOLT J; THIJS L; ZWANENBURG B;
Indirizzi:
CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,NSR CTR MOL STRUCT DESIGN & SYNTH,TOERNOOIVELD NL-6525 ED NIJMEGEN NETHERLANDS CATHOLIC UNIV NIJMEGEN,DEPT ORGAN CHEM,NSR CTR MOL STRUCT DESIGN & SYNTH NL-6525 ED NIJMEGEN NETHERLANDS CATHOLIC UNIV NIJMEGEN,DEPT INORGAN CHEM,NSR CTR MOL STRUCT DESIGN & SYNTH NL-6525 ED NIJMEGEN NETHERLANDS
Titolo Testata:
Journal of the Chemical Society. Perkin transactions. I
fascicolo: 6, , anno: 1997,
pagine: 963 - 967
SICI:
0300-922X(1997):6<963:SACOEN>2.0.ZU;2-2
Fonte:
ISI
Lingua:
ENG
Soggetto:
RING-OPENING REACTIONS; AZIRIDINE-2-CARBOXYLIC ESTERS; AMINO-ACIDS; DERIVATIVES; AZIRIDINES; REAGENTS; PEPTIDES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
39
Recensione:
Indirizzi per estratti:
Citazione:
J.G.H. Willems et al., "SYNTHESIS AND CRYSTAL-STRUCTURE OF ENANTIOPURE N-TRITYLAZIRIDIN-2-YL-METHANOLS FROM L-SERINE AND L-THREONINE", Journal of the Chemical Society. Perkin transactions. I, (6), 1997, pp. 963-967

Abstract

A convenient multigram 'one pot procedure' for the synthesis Of methyl N-tritylaziridine-2-carboxylates 1 and 2, starting from the N-tritylmethyl esters of L-serine 9 and L-threonine 10 and using methanesulfonyl chloride and triethylamine, is described, The N-tritylaziridin-2-ylmethanols 3 and 4 are prepared from the corresponding methyl N-tritylaziridine-2-carboxylates 1 and 2 using a Grignard reaction H-1 and C-13NMR spectral and HPLC chromatographic analysis of aziridine alcohols 3 and 4 have been performed. The crystal structures of compounds 3 and4 reveal that the aziridine ring substituents have the diphenyl-methanol and the trityl groups in a trans relationship and show an intramolecular hydrogen bond between the aziridine nitrogen and the hydroxy group, According to temperature dependent H-1 NMR spectral analysis, a hydrogen bond is also present in solution. The enantiomeric purity of the N-tritylaziridin-2-ylmethanols 3 and 4 has been determined using HPLC techniques.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/11/20 alle ore 10:36:58