Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 16, Pages 7970-7976Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo401161h
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Funding
- National Science Council, Taiwan
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A distinct chemoselectivity in the gold-catalyzed oxidative cyclization of 3,5-dien-1-ynes was observed when 3,5-dichloropyridine N-oxide replaced 8-methylquinoline N-oxide as the oxidant; the resulting cyclopentadienyl aldehydes were obtained in good yields. The altered chemoselectivity is attributed to a prior enyne cyclization in the presence of 3,5-dichloropyridine N-oxides. The use of N-iminopyridium ylide enables a similar iminocyclization reaction to give cyclopentadienyl imines efficiently. Our experimental data support a prior gold-catalyzed cyclization of 3,5-dien-1-ynes to form gold carbene, followed by the oxidation with N-oxide.
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