Enantioselective Rauhut–Currier-Type Cyclizations via Dienamine Activation: Scope and Mechanism

Abstract

This Feature Article describes our mechanistic studies in organocatalytic Rauhut–Currier-type reactions and some applications in target-oriented synthesis. The developed approach involves the cyclization of two tethered Michael acceptors via dienamine intermediates and leads to highly functionalized cycloalkenes. The utility of these intermediates is further demonstrated by the synthesis of biologically important targets, such as optically active iridoid derivatives.

1 Introduction

2 Organocatalytic Cyclization of Tethered α,β-Unsaturated Carbonyl Compounds; Synthesis of Cyclopentene Derivatives

2.1 Mechanistic Proposal

2.1.1 ESI-HRMS Measurements

2.1.2 NMR Experiments

2.1.3 Complementary Reactivity

2.2 Synthetic Applications

3 Organocatalytic Cyclization of Tethered α,β-Unsaturated Carbonyl Compounds; Synthesis of Cyclohexene Derivatives

4 Conclusions

Key words

asymmetric synthesis - organocatalysis - dienamine activation - Rauhut–Currier reaction - Michael addition - reaction mechanisms

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