Osmium(II)-, Rhenium(I)-, and Tungsten(0)-Promoted Dipolar Cycloaddition Reactions with Pyrroles: Exploiting the Azomethine Ylide Character of This Heterocycle
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- 作者：Kevin D. Welch ; Philip L. Smith ; Andrew P. Keller ; William H. Myers ; Michal Sabat ; W. Dean Harman
- 刊名：Organometallics
- 出版年：2006
- 出版时间：October 9, 2006
- 年：2006
- 卷：25
- 期：21
- 页码：5067 - 5075
- 全文大小：170K
- 年卷期：v.25,no.21(October 9, 2006)
- ISSN：1520-6041
文摘
Complexes of the form TpRe(CO)(MeIm)(
2-pyr) and TpW(NO)(PMe3)(2-pyr) (where pyr =1-methylpyrrole, 2-methylpyrrole, and 2,5-dimethylpyrrole) were prepared and combined with a rangeof potential dipolarophiles. In several cases a dipolar cycloaddition resulted in the formation of7-azanorbornene complexes (one crystal structure for each metal is presented), but attempts to developa general route to the organic bicyclic system were unsuccessful. Using the complex [Os(NH3)5(2-pyrrole)]2+ an organic cycloadduct was successfully prepared with dimethyl fumarate, and this complexwas elaborated into advanced synthons to several naturally occurring pyrrolizidines.
2-pyr) and TpW(NO)(PMe3)(2-pyr) (where pyr =1-methylpyrrole, 2-methylpyrrole, and 2,5-dimethylpyrrole) were prepared and combined with a rangeof potential dipolarophiles. In several cases a dipolar cycloaddition resulted in the formation of7-azanorbornene complexes (one crystal structure for each metal is presented), but attempts to developa general route to the organic bicyclic system were unsuccessful. Using the complex [Os(NH3)5(2-pyrrole)]2+ an organic cycloadduct was successfully prepared with dimethyl fumarate, and this complexwas elaborated into advanced synthons to several naturally occurring pyrrolizidines.