Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis

Abstract

Diels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.

1 Introduction

2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis

3 Enantioselective Synthesis of Arene cis-Dihydrodiols by Diels–­Alder/Retro-Diels–Alder Reactions of 2-Pyrones

4 Enantioselective Synthesis of cis-Decalin Derivatives by Diels–­Alder Reactions of 2-Pyrones

5 Conclusions

Key words

pyrones - asymmetric catalysis - Diels–Alder reactions - ­Lewis acid catalysis - natural product synthesis

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