Gold(III) porphyrin-catalyzed cycloisomerization of allenones

Org Lett. 2006 Jan 19;8(2):325-8. doi: 10.1021/ol052696c.

Abstract

[reaction: see text] 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.