Abstract
The roles of chiral bicyclic guanidine, bis-guanidinium and pentanidium in catalysis are presented. Besides the usual Brønsted base reactivity, less known modes of interactions of these catalysts, such as Brønsted base–Brønsted acid and Brønsted–Lewis acid bifunctional activations will be discussed in this account. Pentanidiums are ‘super-guanidines’ with extended conjugation, and their roles in catalysis and halogen bonding will also be elaborated.
Keywords
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- BARF:
-
[B[3,5-(CF3)2C6H3]4]−; Tetrakis(3,5-bis(trifluoromethyl)phenyl) borate
- DBU:
-
1,8-Diazabicycloundec-7-ene
- Eoc:
-
N-3-Ethylpentan-3-yloxycarbonyl
- NHPI:
-
N-Hydroxyphthalimide
- TBD:
-
1,5,7-Triazabicyclo[4.4.0]dec-5-ene
- TBO:
-
1,4,6-Triazabicyclo[3.3.0]oct-4-ene
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Acknowledgements
We wish to thank our dedicated colleagues and collaborators whose names appeared in the citation list. This work is generously funded by National University of Singapore; Nanyang Technological University; Agency for Science, Technology and Research (A*STAR); and GlaxoSmithKline.
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Leow, D., Tan, CH. (2015). Chiral Bicyclic Guanidine, Bis-Guanidinium, Pentanidium and Related Organocatalysts. In: Selig, P. (eds) Guanidines as Reagents and Catalysts I. Topics in Heterocyclic Chemistry, vol 50. Springer, Cham. https://doi.org/10.1007/7081_2015_175
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DOI: https://doi.org/10.1007/7081_2015_175
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