Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates

Yuji Ikeda; Masahito Murai; Tomohiro Abo; Koji Miki; Kouichi Ohe

doi:10.1016/j.tetlet.2007.07.123

Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates

Yuji Ikeda, Masahito Murai, Tomohiro Abo, Koji Miki, Kouichi Ohe

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

We have developed various transition metal-catalyzed vinylcarbene transfer reactions, such as ring-opening, substitution, and cyclopropanation reactions, using O-propargyl thiocarbamates as carbene precursors. Platinum, ruthenium, rhodium, and gold complexes are effective for vinylcarbenoid formation. The highly nucleophilic nature and resonance effect of a thiocarbamoyl moiety readily permit the rearrangement of a thiocarbamoyl moiety from a propargylic position to an adjacent alkynyl carbon to give the intermediary vinylcarbene complexes.

Original language	English
Pages (from-to)	6651-6654
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2007.07.123
Publication status	Published - Sept 17 2007

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates",

abstract = "We have developed various transition metal-catalyzed vinylcarbene transfer reactions, such as ring-opening, substitution, and cyclopropanation reactions, using O-propargyl thiocarbamates as carbene precursors. Platinum, ruthenium, rhodium, and gold complexes are effective for vinylcarbenoid formation. The highly nucleophilic nature and resonance effect of a thiocarbamoyl moiety readily permit the rearrangement of a thiocarbamoyl moiety from a propargylic position to an adjacent alkynyl carbon to give the intermediary vinylcarbene complexes.",

author = "Yuji Ikeda and Masahito Murai and Tomohiro Abo and Koji Miki and Kouichi Ohe",

note = "Funding Information: This work is supported by Grant-in-Aid for Scientific Research on Priority Areas “Synergistic Effects for Creation of Functional Molecules” (Area 459, No. 19027027) and Scientific Research (B, 19350093), from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Financial support from the Sumitomo Foundation is gratefully acknowledged.",

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T1 - Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates

AU - Ikeda, Yuji

AU - Murai, Masahito

AU - Abo, Tomohiro

AU - Miki, Koji

AU - Ohe, Kouichi

N1 - Funding Information: This work is supported by Grant-in-Aid for Scientific Research on Priority Areas “Synergistic Effects for Creation of Functional Molecules” (Area 459, No. 19027027) and Scientific Research (B, 19350093), from the Ministry of Education, Culture, Sports, Science and Technology, Japan. Financial support from the Sumitomo Foundation is gratefully acknowledged.

PY - 2007/9/17

Y1 - 2007/9/17

N2 - We have developed various transition metal-catalyzed vinylcarbene transfer reactions, such as ring-opening, substitution, and cyclopropanation reactions, using O-propargyl thiocarbamates as carbene precursors. Platinum, ruthenium, rhodium, and gold complexes are effective for vinylcarbenoid formation. The highly nucleophilic nature and resonance effect of a thiocarbamoyl moiety readily permit the rearrangement of a thiocarbamoyl moiety from a propargylic position to an adjacent alkynyl carbon to give the intermediary vinylcarbene complexes.

AB - We have developed various transition metal-catalyzed vinylcarbene transfer reactions, such as ring-opening, substitution, and cyclopropanation reactions, using O-propargyl thiocarbamates as carbene precursors. Platinum, ruthenium, rhodium, and gold complexes are effective for vinylcarbenoid formation. The highly nucleophilic nature and resonance effect of a thiocarbamoyl moiety readily permit the rearrangement of a thiocarbamoyl moiety from a propargylic position to an adjacent alkynyl carbon to give the intermediary vinylcarbene complexes.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Transition metal-catalyzed ring-opening, substitution, and cyclopropanation reactions via vinylcarbene complexes generated from O-propargyl thiocarbamates

Abstract

ASJC Scopus subject areas

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