An investigation of the Lewis acid mediated 1,3-dipolar cycloaddition between N-benzyl-C-(2-pyridyl)nitrone and allylic alcohol. Direct entry to isoxazolidinyl C-nucleosides

Autor:	Pedro, Merino, Tomas, Tejero, Mariano, Laguna, Elena, Cerrada, Ana, Moreno, Jose A, Lopez
Rok vydání:	2003
Předmět:	Time Factors Molecular Structure Propanols Reproducibility of Results Nucleosides Stereoisomerism Isoxazoles Crystallography X-Ray Catalysis Models Chemical Cyclization Organometallic Compounds Nitrogen Oxides Acids Oxidation-Reduction
Zdroj:	Organicbiomolecular chemistry. 1(13)
ISSN:	1477-0520
Popis:	The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carried out to obtain the corresponding 2-benzyl-3-(2-pyridyl)-5-hydroxymethylisoxazolidine. The influence of Lewis acids in the reaction has been studied and a complete 3,5-regioselectivity and cis diastereoselectivity was observed when the reaction was carried out with 1.0 equiv of AgOTf, [Ag(OClO3)(PPh2Me)] or Zn(OTf)2. Insight into the mechanism of the reaction has been obtained by isolating and characterizing (X-ray) the intermediate complexes. Also, a model based on both experimental and theoretical results is proposed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=pmid________::f979529f9e387df86ef826485657c503 https://pubmed.ncbi.nlm.nih.gov/12945706 Zobrazit plný text záznamu