Dichloroketene

Leahy, James W.

doi:10.1002/047084289x.rd123

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2023

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“…Following our earlier experience, we employed the tropylium ion with the more lipophilic bis(trifluoromethane)sulfinimide (NTf 2 ) anion because of its better solubility in the applied organic solvents than the commercially available tetrafluoroborate (BF 4 ) form [ 22 – 24 ]. The cyclic urea DMEU (1,3-dimethyl-2-imidazolidinone) [ 26 ] additive was used as polar aprotic solvent, which also increases the homogeneity of the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

Mudráková¹,

Figueiredo²,

Campagne³

et al. 2023

Beilstein J. Org. Chem.

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We present here a stereoselective tandem reaction based on the asymmetric conjugate addition of dialkylzinc reagents to unsaturated acylimidazoles followed by trapping of the intermediate zinc enolate with carbocations. The use of a chiral NHC ligand provides chiral zinc enolates in high enantiomeric purities. These enolates are reacted with highly electrophilic onium compounds to afford densely substituted acylimidazoles. DFT calculations helped to understand the reactivity of the zinc enolates derived from acylimidazoles and allowed their comparison with metal enolates obtained by other conjugate addition reactions.

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Section: Resultsmentioning

confidence: 99%