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Synlett 1995; 1995(SI): 565-567
DOI: 10.1055/s-1995-5289
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Lithium Trifluoromethanesulfonimide in Acetone or Diethyl Ether as a Safe Alternative to Lithium Perchlorate in Diethyl Ether for Effecting Diels-Alder Reactions. Unexpected Influence of the Counterion of Exo/Endo Selectivity

Scott T. Handy, Paul A. Grieco1 , Catherine Mineur, Léon Ghosez2
  • 1Ernest E. Campaigne and Marvin Carmack Laboratory of Organic Chemistry, Department of Chemistry, Indiana University, Bloomington, Indiana 47405 USA
  • 2Laboratoire de Chimie Organique de Synthèse, Université Catholique de Louvain, Place L. Pasteur 1, B-1348 Louvain-la-Neuve, Belgium
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Publication Date:
31 December 2000 (online)

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Concentrated solutions of lithium trifluoromethanesulfonimide in either acetone or diethyl ether constitute convenient and safe alternatives to lithium perchlorate in diethyl ether for promoting and accelerating [4+2] cycloaddition reactions.

Diels-Alder - lithium perchlorate - dienophiles - dienes - lithium trifluoromethanesulfonimide - [4+2] cycloaddition