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

Alberto Fraile; José Alemán

doi:10.1055/s-0034-1380618

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(14): 1940-1954
DOI: 10.1055/s-0034-1380618

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

Alberto Fraile

Departamento de Química Orgánica (módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain eMail: jose.aleman@uam.es URL: www.uam.es/jose.aleman

,

José Alemán*

Departamento de Química Orgánica (módulo 01), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain eMail: jose.aleman@uam.es URL: www.uam.es/jose.aleman

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Abstract

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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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Referenzen

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