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Organoaluminum-mediated Selective 1,2-Rearrangement of γ,γ-Disubstituted γ-Amino α,β-Unsaturated Carbonyl Compounds Leading to Unsymmetrically Substituted Pyrroles by Takashi Ooi; Kohsuke Ohmatsu; Hiroki Ishii; Akira Saito; Keiji Maruoka is a Chemistry article available to read on EtoBox.

What is Organoaluminum-mediated Selective 1,2-Rearrangement of γ,γ-Disubstituted γ-Amino α,β-Unsaturated Carbonyl Compounds Leading to Unsymmetrically Substituted Pyrroles about?

c,c-Dialkyl-c-amino-a,b-unsaturated carbonyl compounds were found to undergo selective skeletal rearrangement under the influence of modified organoaluminum Lewis acid to give unsymmetrically substituted pyrroles through the rapid Paal-Knorr type cyclization upon acidic hydrolysis. This new structural reorganization of amino carbonyl compounds triggered by the 1,2-alkyl shift provides a unique entry to the synthesis of pyrroles, an important class of heterocycles with diverse biological activities.

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Author

Takashi Ooi; Kohsuke Ohmatsu; Hiroki Ishii; Akira Saito; Keiji Maruoka

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2004

Language

EN

Field

Chemistry (Physical Sciences)