Chemical Communications

Iminium ion catalysis: Use of the α-effect in the acceleration of the Diels–Alder reaction

JL Cavill, JU Peters, NCO Tomkinson

Index: Cavill, Julie L.; Peters, Jens-Uwe; Tomkinson, Nicholas C. O. Chemical Communications, 2003 , # 6 p. 728 - 729

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Citation Number: 33

Abstract

It is well established that the nucleophilicity of a heteroatom can be greatly increased by the introduction of an adjacent heteroatom. Known as the α-effect, 8 and rationalised by frontier molecular orbital theory, 9 it has been used to explain the reactivity of a number of systems and has previously been exploited to accelerate synthetic transformations. 10 We believed that we could depart from the constraints inherent to this five membered ring system by taking advantage of the ...