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Letter

Highly Selective Diels−Alder Reactions of Dienophiles with 1,3-Cyclohexadiene Mediated by Yb(OTf)₃·2H₂O and Ultrahigh Pressures

Supporting Info

Aaron C. Kinsman and Michael A. Kerr*

Department of Chemistry, University of Western Ontario, London, Ontario N6A 5B7, Canada

Org. Lett., 2000, 2 (22), pp 3517–3520

DOI: 10.1021/ol0065773

Publication Date (Web): October 4, 2000

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

makerr@julian.uwo.ca

Abstract

Ultrahigh pressures and catalytic Yb(OTf)₃·2H₂O were found to mediate Diels−Alder reactions of various electron-deficient dienophiles with 1,3-cyclohexadiene to produce endo-bicyclo[2.2.2]oct-2-enes in moderate to excellent yield and selectivity. The proposed total synthesis of hapalindole Q based on bicyclo[2.2.2]oct-2-ene construction by Diels−Alder reaction and subsequent olefin cleavage is outlined. Preliminary results demonstrating the viability of this strategy are presented.

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