Synthesis 2018; 50(09): 1773-1782
DOI: 10.1055/s-0037-1609418
short review
© Georg Thieme Verlag Stuttgart · New York

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

Eduarda M. P. Silva*
a  LAQV, REQUIMTE, Department of Chemistry Sciences, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal   Email: [email protected]
b  QOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: [email protected]
,
Djenisa H. A. Rocha
b  QOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: [email protected]
,
b  QOPNA, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal, Email: [email protected]
› Author Affiliations
Thanks are due to University of Aveiro and FCT/MEC for the financial support of the QOPNA research unit (FCTUID/QUI/00062/2013) through national funds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement.
Further Information

Publication History

Received: 28 January 2018

Accepted after revision: 26 February 2018

Publication Date:
04 April 2018 (online)


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

 
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