Ruthenium-catalyzed enantioselective carbon-carbon bond forming reaction via allenylidene-ene process: synthetic approach to chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives.
Our previously disclosed ruthenium-catalyzed carbon-carbon bond forming reactions between propargylic alcohols and alkenes via an allenylidene-ene type pathway have been successfully applied to an enantioselective intramolecular cyclization for a variety of chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives (up to 99% ee) by use of a suitable optically active diruthenium complex as a catalyst. The methodology described in this paper becomes a novel synthetic approach to chiral heterocycles, the structures of which are widely found in many natural and biologically active compounds.
Fukamizu
Koji
K
Institute of Engineering Innovation, School of Engineering, University of Tokyo, Bunkyo-ku, Tokyo 113-8656, Japan.
Miyake
Yoshihiro
Y
Nishibayashi
Yoshiaki
Y
D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D002839:Chromans; D011804:Quinolines; D002244:Carbon; D012428:Ruthenium