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47.1.3.2 Ene Reactions

DOI: 10.1055/sos-SD-047-00294

Chiu, P.; Lam, S. K.Science of Synthesis, (201047737.

General Introduction

The classical Alder-ene, or ene reaction, involves the transfer of an allylic hydrogen from the ene to an unsaturated enophile to form a new CH bond, concomitantly with CC bond formation and double-bond migration (Scheme 1).[‌1‌‌7‌] It is a pericyclic reaction related to the DielsAlder reaction, also involving a six-electron cyclic transition state. A concerted pathway is one limiting mechanism; biradical and zwitterionic pathways for highly polarized ene/enophile combinations are also known.[‌8‌] Compared with the DielsAlder reaction, the activation energy for the ene reaction is much higher; thus, the temperatures required for such reactions are also generally very high.

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References