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Synfacts 2010(6): 0647-0647  
DOI: 10.1055/s-0029-1219983
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Rotaxane Structure Specific Palladium-Catalyzed Rearrangement

Contributor(s): Timothy M. Swager, Stefanie A. Sydlik
N. Miyagawa, M. Watanabe, T. Matsuyama, Y. Koyama, T. Moriuchi, T. Hirao, Y. Furusho, T. Takata*
Tokyo Institute of Technology, Osaka University and Nagoya University, Japan
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Publikationsdatum:
20. Mai 2010 (online)

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Significance

The authors show that a palladium-containing rotaxane accelerates the rearrangement of propargyl and allyl urethanes to oxazoli­dinones. The conversion of allyl urethane 1 into oxazolidinone 2 is accomplished in quantitative yield via two hydroamination reactions of the urethane N-H to the alkene group. The rearrangement of the propargyl urethanes proceeds in much lower yield (16%) since the resulting rigid double bond hinders the translation of the palladium along the rotaxane.