Convenient synthesis of tryptophols and tryptophol homologues by hydroamination of alkynes |
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Authors: | Vivek Khedkar |
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Affiliation: | Leibniz-Institut für Organische Katalyse (IfOK) an der Universität Rostock e.V., Albert-Einstein-Str. 29a, D-18055 Rostock, Germany |
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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 hydrazone, and subsequent deprotection of the hydroxy group. |
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Keywords: | Amination Indoles Catalysis |
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