Synthesis and crystal structure of enantiopure N-tritylaziridin-2-yl-methanols from L-serine and L-threonine Version 4.0

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Synthesis and crystal structure of enantiopure N-tritylaziridin-2-yl-methanols from L-serine and L-threonine
Willems JGH, Hersmis MC, deGelder R, Smits JMM, Hammink JB, Dommerholt J, Thijs L, Zwanenburg B
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (6) 963-967 MAR 21 1997

Document type: Article

Language: English

Cited References: 39

Times Cited: 7

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-13 NMR spectral and HPLC chromatographic analysis of aziridine alcohols 3 and 4 have been performed. The crystal structures of compounds 3 and 4 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.

KeyWords Plus:
RING-OPENING REACTIONS, AZIRIDINE-2-CARBOXYLIC ESTERS, AMINO-ACIDS, DERIVATIVES, AZIRIDINES, REAGENTS, PEPTIDES

Addresses:
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.

Publisher:
ROYAL SOC CHEMISTRY, CAMBRIDGE

IDS Number:
WR332

ISSN:
0300-922X

Article 24 of 38