Fluorous Synthesis of Yuehchukene by α??Lithiation of Perfluoroalkyl??Tagged 1??(Arylsulfonyl) indole with Mesityllithium

H Naka, Y Akagi, K Yamada, T Imahori…

Index: Naka, Hiroshi; Akagi, Yusuke; Yamada, Kyoko; Imahori, Tatsushi; Kasahara, Takahiro; Kondo, Yoshinori European Journal of Organic Chemistry, 2007 , # 28 p. 4635 - 4637

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Citation Number: 16

Abstract

Abstract Lithiation chemistry has not been well explored in fluorous synthesis because of the lack of appropriate base-resistant fluorous tags; we recently developed a perfluoroalkylated arylsulfonyl tag for the protection of the indole ring nitrogen atom. Mesityllithium was found to be a suitable reagent for the α-lithiation of perfluoroalkyl-tagged 1-(arylsulfonyl) indole, and the fluorous synthesis of yuehchukene was accomplished efficiently using this method as ...