Protocols utilizing multi-component coupling reactions followed by various cyclizations have proved to be effective synthetic strategies for diversity oriented synthesis of heterocycles. Herein we report a sequence of Cu(I)-catalyzed three-component coupling followed by enyne metathesis and Heck reaction to form either benzoindolines or cyclopropane-fused tetrahydroindenopyridines in good yields via either 6-endo or 5-exo cyclization pathways. The selectivity for the 6-endo vs 5-exo cyclization pathways is controlled by the rates of subsequent steps. Taking advantage of these divergent pathways, two regioisomeric pyrroloquinolines and 1,7-tetrahydrophenanthroline were also prepared

Diversity oriented synthesis of heterocycles via sequential metal catalysis: Regiodivergent 5-exo vs. 6-endo Heck cyclizations

244th National Meeting (2012)

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