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Secondary and Primary Amine Catalysts for Iminium Catalysis

Part of the Topics in Current Chemistry book series (TOPCURRCHEM,volume 291)

Abstract

Formation of iminium ions from the condensation of chiral secondary or primary amines with a,b-unsaturated aldehydes or ketones can be used as an effective platform for the acceleration of a wide variety of catalytic asymmetric cycloaddition and conjugate addition reactions. The reversible formation of the active iminium ion species simulates the π-electronics and equilibrium dynamics traditionally associated with Lewis acid activation of a,b-unsaturated carbonyl compounds lowering the energy level of the LUMO associated with the π-system and activating subsequent reaction. Importantly, these iminium ion catalysed processes offer the opportunity to conduct reactions in the presence of both moisture and air greatly adding to the practicality and general applicability of the chemistry described. Proposed catalytic cycles and transition state models for the induction of asymmetry provide reliable and robust predictive tools for the outcome of reactions and high functional group tolerance suggests this class of transformation will have broad application in the arena of synthetic organic chemistry as the area matures. This review describes the rapid expansion of iminium ion catalysis over recent years from its conceptual introduction to the development of a whole new arsenal of highly practical and effective methods with which to approach challenging and fundamental bond construction processes.

Keywords

  • Aminocatalysis
  • Conjugate addition
  • Cycloaddition
  • Iminium ion
  • Organocatalysis

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Scheme 73

Abbreviations

Alloc:

Allyloxycarbonyl

DCA:

Dichloroacetic acid

DIPEA:

N,N-Diisopropylethylamine

DNBA:

2,4-Dinitrobenzoic acid

F-SPE:

Fluorous solid phase extraction

HFIP:

1,1,1,3,3,3-Hexafluoro-2-propanol

IMDA:

Intramolecular Diels-Alder reaction

LUMO:

Lowest unoccupied molecular orbital

Ns:

4-Nitrophenylsulfonyl

PMP:

4-Methoxyphenyl

TCA:

Trichloroacetic acid

TES:

Triethylsilyl

TIPBA:

2,4,6-Triisopropylbenzenesulfonic acid

TRIP:

3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate

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Acknowledgments

The authors wish to thank the EPSRC for financial support.

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Brazier, J.B., Tomkinson, N.C.O. (2010). Secondary and Primary Amine Catalysts for Iminium Catalysis. In: List, B. (eds) Asymmetric Organocatalysis. Topics in Current Chemistry, vol 291. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-02815-1_28

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