Abstract
The use of N-heterocyclic carbenes as catalysts for organic transformations has received increased attention in the past 10 years. A discussion of catalyst development and nucleophilic characteristics precedes a description of recent advancements and new reactions using N-heterocyclic carbenes in catalysis.
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Abbreviations
- Ac:
-
acetyl
- Ar:
-
aryl
- BAL:
-
benzaldehyde lyase
- BFD:
-
benzoylformate decarboxylase
- Bmin:
-
butylmethylimidazolium
- Bn:
-
benzyl
- Boc:
-
tert-butoxycarbonyl
- Bz:
-
benzoyl
- Cy:
-
cyclohexyl
- DABCO:
-
1,4-diazabicyclo[1.2.2]octane
- DBU:
-
1,8-diazabicyclo[2.4.0]undec-7-ene
- DCM:
-
dichloromethane
- DIPEA:
-
diisopropylethylamine
- DMF:
-
N,N-dimethylformamide
- DMSO:
-
dimethylsulfoxide
- Et:
-
ethyl
- HOAt:
-
1-hydroxy-7-azabenzotriazole
- i-Pr:
-
isopropyl
- KHMDS:
-
potassium bis(trimethylsiyl)amide
- KPi:
-
buffer potassium phosphate buffer
- Me:
-
methyl
- Mes:
-
mesityl (2,4,6-trimethylphenyl)
- Ms methanesulfonyl (mesyl)MS:
-
molecular sieves
- LiHMDS:
-
lithium bis(trimethylsilyl)amide
- n-Bu:
-
normal-butyl
- n-Hexnormal-hexyln-Pr:
-
normal-propyl
- NHC:
-
N-heterocyclic carbene
- PEMP:
-
pentamethylpiperidine
- Ph:
-
phenyl
- Pr:
-
propyl
- TBS:
-
tert-butyldimethylsilyl
- t-Bu:
-
tert-butyl
- TES:
-
triethylsilyl
- Tf:
-
trifluoromethanesulfonyl (triflyl)
- ThDP:
-
thiamin diphosphate
- THF:
-
tetrahydrofuran
- TIPS:
-
triisopropylsilyl
- TMS:
-
trimethylsilyl
- Tol:
-
para-tolyl
- Ts:
-
para-toluenesulfonyl (tosyl)
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Acknowledgements
The authors thank Jeffrey B. Johnson (Hope College), Javier Read de Alaniz, Mark S. Kerr and the Rovis group (CSU) for their careful reading of the manuscript. Support for our own efforts in this area has been provided by the National Science Foundation (CAREER) and the National Institutes of General Medical Sciences (GM72586). J.L.M. thanks the NIH for the Ruth L. Kirschtein NRSA pre-doctoral fellowship. T.R. thanks Johnson and Johnson, Eli Lilly, and Boehringer Ingelheim for unrestricted support, and the Monfort Family Foundation for a Monfort Professorship. T.R. is a fellow of the Alfred P. Sloan Foundation.
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Moore, J.L., Rovis, T. (2010). Carbene Catalysts. 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_18
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