An Efficient Stereoselective Synthesis of (E)-β-Fluoroalkenyliodonium Salts

Masanori Yoshida; Keiji Kawakami; Shoji Hara

doi:10.1055/s-2004-834857

PAPER

An Efficient Stereoselective Synthesis of (E)-β-Fluoroalkenyliodonium Salts

Masanori Yoshida*, Keiji Kawakami, Shoji Hara*
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, 060-8628, Japan
Fax: +81(11)7066557; e-Mail: myoshida@org-mc.eng.hokudai.ac.jp;

Abstract

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Abstract

Stereoselective synthesis of (E)-β-fluoroalkenyliodonium salts was performed by the treatment of alk-1-ynes with p-iodotoluene difluoride in the presence of HBF₄-Et₂O. The reaction occurred instantaneously at -78 °C to give the fluoroalkenyliodonium salts in good yields with high stereoselectivity. The Pd-catalyzed carbomethoxylation of the fluoroalkenyliodonium salt was also carried out to obtain a (E)-β-fluoro-α,β-unsaturated ester.

Key words

iodonium salt - fluoroalkene - p-iodotoluene difluoride - stereoselective synthesis - fluorination reaction

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Referenzen

References

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