Journal Article Convenient synthesis of spiroindole derivatives via palladium-catalyzed cyclization of propargyl chlorides

Iwata, Akira  ,  Inuki, Shinsuke  ,  Oishi, Shinya  ,  Fujii, Nobutaka  ,  Ohno, Hiroaki

Tetrahedron
71 ( 37 )  , pp.6580 - 6585 , 2015-09 , Elsevier Ltd.
ISSN:0040-4020
NCID:AA00861787
Description
Available online 9 May 2015
Herein, we report the palladium-catalyzed cyclization reactions of indoles bearing a propargyl chloride side chain at their 3-position. In the presence of an external nucleophile, such as a sulfonamide or malonate, indoles bearing a propargyl group at their 3-position gave fused tetracyclic spiroindolines preferentially. However, in the absence of an external nucleophile, the same substrates afforded spiroindoles. Our attempts to develop a catalytic asymmetric spirocyclization onto a propargylpalladium species are also presented in this paper.
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