Bismuth Triflate Catalyzed Allylation of Acetals: A Simple and Mild Method for Synthesis of Homoallyl Ethers

Ram S. Mohan; Laura C. Wieland; Herbert M. Zerth

Bismuth Triflate Catalyzed Allylation of Acetals: A Simple and Mild Method for Synthesis of Homoallyl Ethers

Ram S. Mohan, Laura C. Wieland, Herbert M. Zerth

Illinois Wesleyan University

Research output: Journal Article › Article › peer-review

Abstract

The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.

Original language	American English
Journal	Tetrahedron
Volume	43
State	Published - 2002

Keywords

Bismuth and compounds
Lewis acid.
allylation
homoallyl ethers

Disciplines

Organic Chemistry

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Cite this

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title = "Bismuth Triflate Catalyzed Allylation of Acetals: A Simple and Mild Method for Synthesis of Homoallyl Ethers",

abstract = " The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.",

keywords = "Bismuth and compounds, Lewis acid., allylation, homoallyl ethers",

author = "Mohan, {Ram S.} and Wieland, {Laura C.} and Zerth, {Herbert M.}",

year = "2002",

language = "American English",

volume = "43",

journal = "Tetrahedron",

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TY - JOUR

T1 - Bismuth Triflate Catalyzed Allylation of Acetals: A Simple and Mild Method for Synthesis of Homoallyl Ethers

AU - Mohan, Ram S.

AU - Wieland, Laura C.

AU - Zerth, Herbert M.

PY - 2002

Y1 - 2002

N2 - The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.

AB - The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.

KW - Bismuth and compounds

KW - Lewis acid.

KW - allylation

KW - homoallyl ethers

M3 - Article

VL - 43

JO - Tetrahedron

JF - Tetrahedron

ER -