Regioselective synthesis of highly substituted furans via tantalum-alkyne complexes.

Yasutaka Kataoka; Makoto Tezuka; Kazuhiko Takai; Kiitiro Utimoto

doi:10.1016/S0040-4020(01)88488-X

Regioselective synthesis of highly substituted furans via tantalum-alkyne complexes.

Yasutaka Kataoka, Makoto Tezuka, Kazuhiko Takai, Kiitiro Utimoto

Research output: Contribution to journal › Article

19 Citations (Scopus)

Abstract

A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with a aldehydes followed by addition of an isocyanide in DME-PhH-THF (1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on a acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substitued furans are produced exclusively when trialkylsilylacetylenes are employed.

Original language	English
Pages (from-to)	3495-3502
Number of pages	8
Journal	Tetrahedron
Volume	48
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(01)88488-X
Publication status	Published - 1992
Externally published	Yes

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Keywords

Tantalum
furan
isocyanide
metal-alkyne complex
niobium

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Kataoka, Y., Tezuka, M., Takai, K., & Utimoto, K. (1992). Regioselective synthesis of highly substituted furans via tantalum-alkyne complexes. Tetrahedron, 48(17), 3495-3502. https://doi.org/10.1016/S0040-4020(01)88488-X

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abstract = "A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with a aldehydes followed by addition of an isocyanide in DME-PhH-THF (1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on a acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substitued furans are produced exclusively when trialkylsilylacetylenes are employed.",

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AU - Kataoka, Yasutaka

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PY - 1992

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N2 - A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with a aldehydes followed by addition of an isocyanide in DME-PhH-THF (1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on a acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substitued furans are produced exclusively when trialkylsilylacetylenes are employed.

AB - A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with a aldehydes followed by addition of an isocyanide in DME-PhH-THF (1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on a acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substitued furans are produced exclusively when trialkylsilylacetylenes are employed.

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KW - isocyanide

KW - metal-alkyne complex

KW - niobium

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10.1016/S0040-4020(01)88488-X