Solid-Supported [2+2+2] Cyclotrimerizations Catalyzed by Rh and Ru

D. D. Young; R. S. Senaiar; A. Deiters

doi:10.1055/s-2006-949298

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Synfacts 2006(10): 1079-1079
DOI: 10.1055/s-2006-949298

Polymer-Supported Synthesis

Solid-Supported [2+2+2] Cyclotrimerizations Catalyzed by Rh and Ru

Contributor(s): Yasuhiro Uozumi, Yohei Oe
D. D. Young, R. S. Senaiar, A. Deiters*
North Carolina State University, Raleigh, USA

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Publikationsverlauf

Publikationsdatum:
21. September 2006 (online)

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Significance

The reaction of polystyrene-supported dipropargylamine 1 with alkyne 2 in the presence of RhCl(PPh₃)₃ gave the cyclotrimerization product 3. Treatment of 3 with HCl yielded isoindolines 4 in 69-95% yield as HCl salts (eq. 1). Cyclotrimerization of diynes 5 with 2 in the presence of RhCl(PPh₃)₃ followed by cleavage from the polystyrene support afforded indanes 7 in 60-84% yield (eq. 2). Cyclotrimerization of 8 with 2 in the presence of RuCl(cod)Cp* as catalyst followed by treatment with K₂CO₃ gave the phthalans 10 in 68-95% yield with good regioselectivity (eq. 3).