863890-08-8Relevant academic research and scientific papers
Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes
Khedkar, Vivek,Tillack, Annegret,Michalik, Manfred,Beller, Matthias
, p. 7622 - 7631 (2005)
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 hydrazone, and subsequent deprotection of the hydroxy group.
