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N-苄基-C-(2-吡啶基)硝酮与烯丙醇之间路易斯酸介导的1,3-偶极环加成反应的研究。直接合成异恶唑烷基亚甲基碳核苷。

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.

作者信息

Merino Pedro, Tejero Tomas, Laguna Mariano, Cerrada Elena, Moreno Ana, Lopez Jose A

机构信息

Departamento de Quimica Organica Facultad de Ciencias, ICMA, Universidad de Zaragoza, CSIC, E-50009 Zaragoza, Aragon, Spain.

出版信息

Org Biomol Chem. 2003 Jul 7;1(13):2336-42. doi: 10.1039/b304112c.

DOI:10.1039/b304112c
PMID:12945706
Abstract

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.

摘要

进行了N-苄基C-(2-吡啶基)硝酮与烯丙醇的环加成反应，以获得相应的2-苄基-3-(2-吡啶基)-5-羟甲基异恶唑烷。研究了路易斯酸在该反应中的影响，当反应使用1.0当量的三氟甲磺酸银、[Ag(OClO3)(PPh2Me)]或三氟甲磺酸锌进行时，观察到了完全的3,5-区域选择性和顺式非对映选择性。通过分离和表征（X射线）中间体配合物，对反应机理有了深入了解。此外，还提出了一个基于实验和理论结果的模型。

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