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Letter

Gold(III) Porphyrin-Catalyzed Cycloisomerization of Allenones

Supporting Info

Cong-Ying Zhou, Philip Wai Hong Chan, and Chi-Ming Che*

Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong

Org. Lett., 2006, 8 (2), pp 325–328

DOI: 10.1021/ol052696c

Publication Date (Web): December 18, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, cmche@hku.hk

Abstract

Gold(III) porphyrin-catalyzed cycloisomerization of allenones gave the corresponding furans in good to excellent yields (up to 98%) and with quantitative substrate conversions. By recovering the Au(III) catalyst, a recyclable catalytic system is developed with over 8300 product turnovers attained for the cycloisomerization of 1-phenyl-buta-2,3-dien-1-one. The versatility of the gold(III) porphyrin catalyst was exemplified by its application to the hydroamination and hydration of phenylacetylene in 73% and 87% yield, respectively.

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