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Synfacts 2011(6): 0651-0651  
DOI: 10.1055/s-0030-1260442
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rapid Access to Stereochemically Defined Heterocyclic Scaffolds

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
T. D. Nguyen, R. Webster, M. Lautens*
University of Toronto, Canada
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

This work describes the rhodium(I)-mediated ring opening of hetaryne-furan Diels-­Alder adducts, the unexplored class of compounds in the context of transition-metal catalysis. Various types of heterocyclic substrates 2-5 have been screened. The resulting derivatives are interesting as being analogous to bioactive products (2-aminotetralins), and thus can be used in diversity-oriented synthesis of potential drug ­candidates.