Rate Enhancement Effects in the Dabco Catalysed Synthesis of Hydroxyalkenoate Esters

Ameer, Farouk; Drewes, Siegfried E.; Freese, Susan; Kaye, Perry T.

doi:10.1080/00397918808060742

Cited by 110 publications

(37 citation statements)

References 7 publications

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“…MBH reactions of certain substrates occur quite slowly. Many experiments showed that the protonic solvents such as methanol, ethanol, etc., can accelerate MBH reactions 12–18. Kaye, Marko, and Ikegami suggested that the protonic solvent can accelerate the CC bond formation process by activating the aldehyde through hydrogen bond 17–19.…”

Section: Introductionmentioning

confidence: 99%

DFT study on the role of methanol solvent in Morita–Baylis–Hillman reaction

Fan¹,

Yang²,

He³

2009

Int J of Quantum Chemistry

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B3LYP/6-311ϩϩG** calculations have been carried out to study the role of methanol solvent in the trimethylamine-catalyzed Morita-Baylis-Hillman reaction between acraldehyde and formaldehyde with CPCM solvent method and supramolecular model with one explicit CH 3 OH solvent molecule, respectively. The optimized geometries and energies of the reactant complexes, intermediates, transition states, and products of the two reaction channels (corresponding to the scenarios of synand anti-acraldehyde, respectively) were obtained, and the relative energy profiles were completed. The results reveal that CH 3 OH solvent molecules can stabilize the zwitterionic intermediates and largely reduce the barrier of H transfer process by taking part in the formation of the transition state in this process. COC bond formation step is the rate-determining step of the whole reaction cycle.

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Section: Introductionmentioning

confidence: 99%

DFT study on the role of methanol solvent in Morita–Baylis–Hillman reaction

Fan¹,

Yang²,

He³

2009

Int J of Quantum Chemistry

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“…The use of DABCO and DMAP gave better results than those of other catalysts including triphenylphosphine and triethylamine (Table 1, entries [10][11][12]. No product was observed when triethylamine was used.…”

Section: Resultsmentioning

confidence: 97%

An Efficient and Recyclable DMAP-Based Ionic Liquid/Water System for Morita–Baylis–Hillman Reactions

Zhang

et al. 2012

Journal of Chemical Research

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“…This structure provides rigidity to the postulated activated complex and thus allows a higher selectivity. [69] In this arrangement the conformation is nearly ideal for the subsequent elimination process that is necessary for the regeneration of the catalyst. Phosphorus-based chiral molecules also mediate the asymmetric Baylis ± Hillman transformation efficiently.…”

Section: The Enantioselective Catalytic Baylis ± Hillmanmentioning

confidence: 99%