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-Tetra

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• 作者：Koji Fukamizu ; Yoshihiro Miyake ; Yoshiaki Nishibayashi
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：August 13, 2008
• 年：2008
• 卷：130
• 期：32
• 页码：10498-10499
• 全文大小：158K
• 年卷期：v.130,no.32(August 13, 2008)
• ISSN：1520-5126

文摘

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.