A copper-catalyzed domino radical cyclization route to benzospiro-indolizidinepyrrolidinones |
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Authors: | Christian V. Stevens,Ellen Van Meenen,Yves Eeckhout,Bart D&rsquo hondt,Viktor V. Zhdankin |
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Affiliation: | a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium b Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA |
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Abstract: | In this Letter the synthesis of benzospiro-indolizidinepyrrolidinones is described by a domino atom transfer radical cyclization reaction using a copper catalyst. The structure of one of the products was established by single crystal X-ray diffraction. The investigated precursors, bearing a homo allyl substituent on the N-indole, result in a 5-exo-trig, followed by a 6-endo-trig cyclization. When the N-indole is substituted with an allyl group, only the spiro-cyclization occurs. |
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Keywords: | Cu(I)Cl Atom transfer radical cyclization ATRC Domino reaction |
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