Indolecarbonyl coupling reactions promoted by samarium diiodide. Application to the synthesis of indole-fused compounds

…, FD Yang, JS Shiue, SM Yang, JM Fang

Index: Lin, Shu-Chen; Yang, Fwu-Duo; Shiue, Jiann-Shyng; Yang, Shyh-Ming; Fang, Jim-Min Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 2909 - 2917

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Citation Number: 36

Abstract

By the assistance of an N-sulfonyl group or a cyano group at the C-2 position, hydroxyalkylations of indole-3-carbonyls were achieved by the promotion of samarium diiodide. The indolecarbonyl coupling reactions proceeded in high stereoselectivity via chelate transition states. Intramolecular indolecarbonyl couplings of 1-(3-oxopropyl) indole-3- carboxaldehydes were realized as the indolecarbonyl group was more reactive toward ...

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