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Carbene Catalysis: Beyond the Benzoin and Stetter Reactions

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Inventing Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 44))

Abstract

The discovery and development of new N-heterocyclic carbene-catalyzed reaction is described. Based on inspiration from nature, we have taken thiazolium-based approaches to umpolung reactivity and invented a suite of related reactions involving acyl anions, homoenolate, and enolate nucleophiles all generated under catalytic conditions.

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Abbreviations

Ar:

Aryl

Bn:

Benzyl

Cy:

Cyclohexyl

DABCO:

1,4-Diazabicyclo[2,2,2]octane

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCM:

Dichloromethane

DMAP:

N,N-4-dimethylaminopyridine

E+ :

Electrophile

Ee:

Enantiomeric excess

Et:

Ethyl

H:

Hour

HOMO:

Highest occupied molecular orbital

i-Pr:

iso-Propyl

L.A.:

Lewis acid

Me:

Methyl

Mes:

Mesityl

NHC:

N-heterocyclic carbene

NMR:

Nuclear magnetic resonance

Np:

Naphthyl

Nu− :

Nucleophile

p :

Para

Ph:

Phenyl

Pr:

Propyl

TADDOL:

2,2-Dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol

TBD:

1,5,7-Triazabicyclo[4.4.0]dec-5-ene

TBDPS:

tert-Butyldiphenylsilyl

t-Bu:

tert-Butyl

Tf:

Trifluoromethanesulfonyl

THF:

Tetrahydrofuran

Tol:

Tolyl

Ts:

p-Toluenesulfonyl

X− :

Counterion

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Acknowledgments

We gratefully acknowledge Northwestern University, the National Institute of General Medical Sciences (R01GM73072), the Sloan Foundation, Abbott Laboratories, Amgen, AstraZeneca, Boehringer-Ingelheim, GlaxoSmithKline, and Novartis for their generous support of our research program. FQRNT (Fonds québécois de la recherche sur la nature et les technologies) is also gratefully acknowledged for a postdoctoral fellowship to B.C.D. Lastly, we thank all current and former Scheidt group members for their heartfelt dedication and lasting contributions.

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Authors and Affiliations

  1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, Evanston, IL, 60208, USA

    Benoit Cardinal-David & Karl A. Scheidt

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  1. Benoit Cardinal-David
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  2. Karl A. Scheidt
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Correspondence to Karl A. Scheidt .

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  1. , FB Chemie - Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Str. 54, Kaiserslautern, 67663, Germany

    Lukas J. Gooßen

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Cardinal-David, B., Scheidt, K.A. (2012). Carbene Catalysis: Beyond the Benzoin and Stetter Reactions. In: Gooßen, L. (eds) Inventing Reactions. Topics in Organometallic Chemistry, vol 44. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_2012_47

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