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Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade
Authors:Tomohiro Fujii  Yuta Oki  Masahisa Nakada
Affiliation:Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
Abstract:The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a transtrans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2?h at room temperature in the presence of a suitable thioester. The developed protocol as well as the prepared chiral compounds are useful for the enantioselective total synthesis of terpenoids with the transtrans-cis fused ring system.
Keywords:Liebeskind-Srogl  Intramolecular  Diels-Alder  Cascade  Stereoselective
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