An efficient and simple Morita–Baylis–Hillman reaction based on the N-methylpyrrolidine–Ba(OH) 2 catalytic system

By using of precise catalytic amount of N-methylpyrrolidine (5 mol %) and Ba(OH) 2 (1.5 mol %) in H 2O/CH 3OH 5/1 or CH 3OH/CH 2Cl 2 3/1 solvent mixtures at T=0 °C a Morita–Baylis–Hillman derivatives could be obtained in good to excellent yield from 2-cyclopenten-1-one, 2-cyclohexen-1-one and formal...

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Bibliographic Details
Published in:Tetrahedron 2011-04, Vol.67 (14), p.2562-2569
Main Authors: Guerra, Krassimira P., Afonso, Carlos A.M.
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Cooperative catalysis
Enone
Exact sciences and technology
Formaldehyde
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
MBH reaction
N-Methylpyrrolidine
Organic chemistry
Preparations and properties
Water
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Summary:By using of precise catalytic amount of N-methylpyrrolidine (5 mol %) and Ba(OH) 2 (1.5 mol %) in H 2O/CH 3OH 5/1 or CH 3OH/CH 2Cl 2 3/1 solvent mixtures at T=0 °C a Morita–Baylis–Hillman derivatives could be obtained in good to excellent yield from 2-cyclopenten-1-one, 2-cyclohexen-1-one and formaldehyde and diverse aryl aldehydes after suitable reaction time. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.02.020