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DOI: 10.1055/s-0036-1588453
Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis
Financial support for this research was provided by the National Institutes of Health (GM 46503) and the National Science Foundation (CHE-1212446 and CHE-1464690)Publikationsverlauf
Received: 03. April 2017
Accepted after revision: 15. Mai 2017
Publikationsdatum:
05. Juli 2017 (online)
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Published as part of the ISHC Conference Special Section
Abstract
Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring heterocycles through asymmetric [3+3] cycloaddition are reported. Asymmetric organocatalysis uses chiral amines, thioureas, phosphoric acids, or NHC catalysis to achieve high enantiocontrol. Transition-metal catalysts used as chiral Lewis acids to activate a dipolar species is an alternative approach. The most recent advance, chiral transition-metal-catalyzed reactions of enoldiazo compounds, has contributed toward the versatile and highly selective synthesis of six-membered heterocyclic compounds.
1 Introduction
2 Asymmetric Formal [3+3]-Cycloaddition Reactions by Organocatalysis
2.1 By Amino-Catalysis
2.2 By N-Heterocyclic Carbenes
2.3 By Bifunctional Tertiary Amine-thioureas
2.4 By Chiral Phosphoric Acids
3 Asymmetric Formal [3+3]-Cycloaddition Reactions by Transition-Metal Catalysis
3.1 Copper Catalysis
3.2 Other Transition-Metal Catalysis
4 Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazo Compounds
4.1 Asymmetric [3+3]-Cycloaddition Reactions of Nitrones with Electrophilic Metallo-enolcarbene Intermediates
4.2 Dearomatization in Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazoacetates
4.3 Asymmetric Stepwise [3+3]-Cycloaddition Reaction of Enoldiazoacetates with Hydrazones
5 Summary and Outlook
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