Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes

V Khedkar, A Tillack, M Michalik, M Beller

Index: Khedkar, Vivek; Tillack, Annegret; Michalik, Manfred; Beller, Matthias Tetrahedron, 2005 , vol. 61, # 32 p. 7622 - 7631

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Citation Number: 67

Abstract

A novel method is presented for the one-pot synthesis of substituted 3-(2-hydroxyethyl)-and 3-(3-hydroxypropyl) indoles (tryptophols and homotryptophols) from aryl hydrazines and silyl- protected ω-(hydroxyoalkyl) alkynes. Various tryptophol derivatives were prepared directly in good yield with excellent regioselectivity via a domino reaction sequence consisting of a titanium-catalyzed hydroamination of the alkyne,[3+ 3]-rearrangement of the resulting aryl ...