Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides

Authors:	Markus Sterk Willi Bannwarth

Affiliation:	Institut für Organische Chemie, Albert‐Ludwigs‐Universit?t Freiburg, Albertstra?e 21, DE‐79104 Freiburg (fax: +49‐761‐2038705)

Abstract:	We describe the modulation of reactivities of dienophiles for Diels? Alder reactions via a new principle based on chelating amides positioned adjacent to their C?C bond. It is demonstrated for modified acrylic acid derivatives and related dienophiles with three different chelating entities. Complexation of the chelators leads to an intensified electron‐withdrawing effect leading to an enhancement of reactivity in Diels? Alder reactions depending on the complexed metal ion. The application of this new approach might be extended to other reactions with reacting entities adjacent to chelating amides.

Keywords:	Cycloadditions Chelates Amides Diels Alder reaction