Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 69, Issue 19, Pages 6419-6426Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo049429p
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- NIGMS NIH HHS [GM-52491] Funding Source: Medline
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A Kumada cross-coupling reaction involving organomagnesium reagents and (3-methylthio-2-azaallyl)stannanes with a Ni(O) catalyst provided cyclic nonstabilized (2-azaallyl)stannanes in moderate to good yields. Primary alkyl, aryl, and allylic organomagnesium reagents can be used as the cross-coupling partner. In general, NiCl(2)dppp in toluene at room temperature provided the shortest reaction times and most consistent yields. The azomethine ylides and 2-azaallyllithium species derived from these stannanes were shown to undergo efficient [3 + 2] cycloaddition reactions to provide azabicyclo[n.2.1] alkanes as the endo cycloadducts. These cycloadducts were found to be useful as starting materials for further elaboration into aza-bridged bicyclic natural and unnatural products of biological interest. Although cyclic 2-azaallyllithium species have been generated previously, this work reports the first generation and cycloaddition of entirely nonstabilized 2-azaallyllithium species. In addition a novel extension of the Kumada coupling was developed to allow for the preparation of the cyclic (2-azaallyl)stannanes, which are precursors to the nonstabilized 2-azaallyllithium species.
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