Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines

Eduarda M. P. Silva; Djenisa H. A. Rocha; Artur M. S. Silva

doi:10.1055/s-0037-1609418

Synthesis, Table of Contents

Synthesis 2018; 50(09): 1773-1782
DOI: 10.1055/s-0037-1609418

short review

Diels–Alder Reactions of 1,2-Dihydropyridines: An Efficient Tool for the Synthesis of Isoquinuclidines

Eduarda M. P. Silva*

^aLAQV, REQUIMTE, Department of Chemistry Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal Email: esilva@ff.up.pt

^bQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: artur.silva@ua.pt

,

Djenisa H. A. Rocha

^bQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: artur.silva@ua.pt

,

Artur M. S. Silva *

^bQOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: artur.silva@ua.pt

› Author Affiliations

Abstract

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Abstract

The Diels–Alder reaction of 1,2-dihydropyridines with different dienophiles is a well-established and straightforward method for the synthesis of isoquinuclidines. Nevertheless, the enantioselective preparation of isoquinuclidines using organocatalysts or organometallic catalysts is rather unexplored. This succinct review offers readers an overall perspective of the most important recent developments and concepts related to this topic.

1 Introduction

2 Asymmetric Diels–Alder Reaction of 1,2-Dihydropyridines

2.1 Transition-Metal-Catalyzed Reactions

2.2 Organocatalyzed Reactions

3 Diels–Alder Reaction of 1,2-Dihydropyridines in the Synthesis of Biologically Valuable Compounds

4 Conclusion

Key words

organocatalysis - organometallic catalysis - asymmetric transformations - enantioselective reactions - Lewis acids - alkaloids - ibogaine - Tamiflu

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References

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