Inter- and Intramolecular Dienamine Organocatalytic Strategies for the Synthesis of Tetrahydroisoquinolines and Tricyclic Derivatives via [3+2] and [4+2] Cycloadditions

Abstract

The use of dienamines represents a new approach for carrying out asymmetric aminocatalytic reactions controlled by a remote chiral catalyst. In this account, we describe our contributions on the use of dienamine methodologies for the synthesis of interesting compounds from a natural product and pharmaceutical point-of-view. Dienamine aminocatalysis is employed for the synthesis of tetrahydroisoquinoline derivatives via intermolecular [3+2] cycloadditions, and for the preparation of tricyclic products by means of intramolecular [4+2] Diels–Alder reactions.

1 Introduction

2 Intermolecular Dienamine versus Iminium Ion Catalysis: Synthesis of Tetrahydroisoquinoline Derivatives

3 Intramolecular Dienamine Catalysis: Synthesis of Tricyclic Derivatives

4 Outlook

Key words

organocatalysis - dienamines - iminium ions - tetrahydroisoquinolines - tricyclic derivatives

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