Traceless stereoinduction in the one-pot synthesis of hexahydrodibenzopyrans

ORGN 321

Keith A. Korthals, kkorthals@hotmail.com and William D. Wulff, wulff@chemistry.msu.edu. Department of Chemistry, Michigan State University, East Lansing, MI 48824-1322
We report a benzannulation from a Fischer carbene complex and a propargyl ether to construct a tricyclic system (hexahydrodibenzopyrans) in one pot with modest to good yields. This is the first time such a Dötz reaction with a intramolecular, tandom Diels-Alder reaction has been reported. Further, we were able to induce chirality (up to 98 % ee) at the bridge head for the formation of hexahydrodibenzopyrans via a traceless central-to-planar-to-central chiral relay.