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Synfacts 2007(12): 1328-1328  
DOI: 10.1055/s-2007-991386
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase [2+2+2] Cycloaddition of Resin-Bound Dipropargylamine with Alkynes

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
M. Shanmugasundaram, A. L. Aguirre, M. Leyva, B. Quan, L. E. Martinez*
University of Texas at el Paso, USA
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

The resin-bound dipropargylamine 3 was prepared by treatment of commercially available trityl chloride resin 1 with dipropargyl­amine 2 using N,N-diisopropylethylamine as a base. The microwave-assisted iridium-catalyzed [2+2+2] cycloaddition of 3 with several alkynes 4, followed by TFA cleavage and catch-release purification with basic alumina of resin-bound intermediates 5, gave the corresponding salt-free isoindoline derivatives 6 in 50-70% yields.