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Gold(III) Porphyrin-Catalyzed Cycloisomerization of Allenones

Organic LettersPublished 18 December 2005
Cong‐Ying Zhou, Philip Wai Hong Chan, Chi‐Ming Che
Citations290
SJR quartileQ1
SJR score1.24
SNIP1.03

TL;DR

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.

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.

Keywords

ChemistryBiochemistry, Genetics and Molecular Biology