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[4 + 2]环缩合反应的钨-二氢吡啶配合物和生成的三取代和四取代哌啶。

[4 + 2] Cyclocondensation reactions of tungsten-dihydropyridine complexes and the generation of tri- and tetrasubstituted piperidines.

机构信息

Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904, United States.

出版信息

J Am Chem Soc. 2011 Nov 16;133(45):18378-87. doi: 10.1021/ja2075086. Epub 2011 Oct 26.

DOI:10.1021/ja2075086
PMID:21961580
Abstract

A new method for the preparation of functionalized piperidines is described in which various dihydropyridine (DHP) complexes of {TpW(NO)(PMe(3))} that are derived from pyridine-borane undergo [4 + 2] cyclocondensation with enones, enals, nitrosobenzene, and several isocyanates to form [2.2.2] bicyclic species. In several cases the diazabicyclooctene products derived from DHP complexes and isocyanates can be further elaborated into novel syn-2,5-disubstituted and 2,3,6-trisubstituted piperidinamides.

摘要

一种新的制备功能化哌啶的方法被描述，其中各种二氢吡啶（DHP）配合物{TpW（NO）（PMe3）}衍生自吡啶-硼烷，与烯酮、烯醛、亚硝基苯和几种异氰酸酯发生[4+2]环缩合反应，形成[2.2.2]双环物种。在几种情况下，DHP 配合物和异氰酸酯衍生的二氮杂双环辛烯产物可以进一步衍生为新型的顺式-2,5-二取代和 2,3,6-三取代哌啶酰胺。

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