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Synthesis 2017; 49(12): 2605-2620
DOI: 10.1055/s-0036-1589003
DOI: 10.1055/s-0036-1589003
short review
Enantioselective Catalytic Methods for the Elaboration of Chiral Tetrahydro-β-carbolines and Related Scaffolds
Weitere Informationen
Publikationsverlauf
Received: 07. Februar 2017
Accepted after revision: 27. März 2017
Publikationsdatum:
02. Mai 2017 (online)
Abstract
Tetrahydro-β-carbolines are important synthetic intermediates in the total synthesis of natural products and of compounds exhibiting strong bioactivities. Over the last decades, catalytic methods using chiral catalysts have been described for their synthesis. This review covers catalytic and enantioselective methods to access chiral tetrahydro-β-carbolines and their applications in the elaboration of complex chiral molecules.
1 Introduction
2 Asymmetric Reduction of Dihydro-β-carbolines
2.1 Asymmetric Transfer Hydrogenation Reactions
2.2 Asymmetric Hydrogenation Reactions
2.3 Biocatalyzed Reduction of Dihydro-β-carbolines
3 Organocatalyzed Pictet–Spengler Reactions
3.1 Chiral Thiourea-Catalyzed Reactions
3.2 Chiral Phosphoric Acid Catalyzed Reactions
4 Pictet–Spengler Reactions of In Situ Generated Cyclic Iminiums
5 Organocatalyzed Functionalization of Dihydro-β-carboliniums
6 Organocatalyzed Alkylation of Tetrahydro-β-carbolines
7 Biocatalyzed Dynamic Kinetic Resolution of Tetrahydro-β-carbolines
8 Conclusion and Perspectives
-
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For some examples using chiral oxaborolidines, chiral borohydrides, or calix[6]arenes/NaBH4, see:
For enantioselective Pictet–Spengler reactions using stoichiometric chiral borane reagents, see:
For representative examples of diastereoselective methods, see:
For the use of chiral auxiliaries, see:
For representative examples, see: