InCl3-Catalyzed [3 + 2] Cycloaddition Reactions: A Facile Synthesis of trans-Dihydrobenzofurans and Substituted Cyclobutane Derivatives

J. S. Yadav; B. V. S. Reddy; G. Kondaji

doi:10.1055/s-2003-39175

PAPER

InCl₃-Catalyzed [3 + 2] Cycloaddition Reactions: A Facile Synthesis of trans-Dihydrobenzofurans and Substituted Cyclobutane Derivatives

J. S. Yadav*, B. V. S. Reddy, G. Kondaji
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.ap.nic.in;

Abstract

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Abstract

1,4-Benzoquinones undergo smoothly [3 + 2] cycloaddition reactions with electron rich alkenes in the presence of 10 mol% indium trichloride or 5 mol% iodine under mild conditions to afford the corresponding 2,3-dihydrobenzofurans in excellent yields with trans-selectivity. Similarly, methyl vinyl ketone reacts with electron rich olefins to produce substituited trans-cyclobutane derivatives.

Key words

indium reagents - iodine - p-quinones - alkenes - benzofurans

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References

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