Facile synthesis of 3-alkoxyindoles via rhodium (II)-catalysed diazoindole O–H insertion reactions

JG Kettle, AW Faull, SM Fillery, AP Flynn, MA Hoyle…

Index: Kettle; Faull; Fillery; Flynn; Hoyle; Hudson Tetrahedron Letters, 2000 , vol. 41, # 35 p. 6905 - 6907

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Citation Number: 16

Abstract

As part of an ongoing research program, we sought to develop an efficient general approach to the synthesis of 3-alkoxyindoles 2. 1 Transition metal-catalysed carbenoid insertion of α-diazoketones into alcohols has become a powerful method for the synthesis of α-alkoxyketones and related compounds. 2 We reasoned that 2-carboethoxy-3-diazo-3H-indole 1 could act as a substrate for this reaction as it is isoelectronic with α-diazocarbonyl compounds 3 (Scheme 1) and ...