2, 3-Disubstituted indoles from olefins and hydrazines via tandem hydroformylation–Fischer indole synthesis and skeletal rearrangement

P Linnepe, AM Schmidt, P Eilbracht

Index: Linnepe, Petra; Schmidt, Axel M.; Eilbracht, Peter Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 302 - 313

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Citation Number: 59

Abstract

The tandem hydroformylation–Fischer indolisation protocol is used in the synthesis of 2, 3- disubstituted indoles. After hydroformylation of selected olefins to form α-branched aldehydes in a one-pot procedure these are condensed with phenylhydrazine to give hydrazones. Upon acid-promoted [3, 3]-sigmatropic rearrangement indolenine intermediates with quaternary centres in the 3-position are formed, which, after selective Wagner– ...