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Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

ABSTRACT: Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.

SUBMITTER: Liu R 

PROVIDER: S-EPMC3884031 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Liu Renhe R   Winston-McPherson Gabrielle N GN   Yang Zhong-Yue ZY   Zhou Xin X   Song Wangze W   Guzei Ilia A IA   Xu Xiufang X   Tang Weiping W  

Journal of the American Chemical Society 20130523 22

Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes. ...[more]

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