Efficient Tandem Morita-Baylis-Hillman/Double Cross-Aldol Reaction between Cyclic Enones and Formaldehyde Promoted by N-Methylpyrrolidine

The Lewis base N‐methylpyrrolidine acts in water as an efficient promoter of tandem reactions between 2 cyclopenten‐1‐one and aqueous formaldehyde. The reaction pathway includes, as consecutive independent steps, a MBH reaction and a double cross‐aldol reaction to furnish the new 2,5,5‐tris(hydroxym...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2011-04, Vol.2011 (12), p.2372-2379
Main Authors: Guerra, Krassimira P., Afonso, Carlos A. M.
Format: Article
Language:English
Subjects:
Aldehydes
Aldol reactions
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Allylic compounds
Chemistry
Domino reactions
Enones
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Summary:The Lewis base N‐methylpyrrolidine acts in water as an efficient promoter of tandem reactions between 2 cyclopenten‐1‐one and aqueous formaldehyde. The reaction pathway includes, as consecutive independent steps, a MBH reaction and a double cross‐aldol reaction to furnish the new 2,5,5‐tris(hydroxymethyl)‐2‐cyclopenten‐1‐one in excellent yield. A range of cyclic enones and 4‐nitrobenzaldehyde undergo the tandem reaction similarly. The reaction mechanism was also investigated. A simple environmentally friendly domino Morita–Baylis–Hillman (MBH) cross‐aldol addition reaction in water with 2‐cyclopent‐1‐one or other cyclic enones and formaldehyde as partners is disclosed. The novel 2,5,5‐tris‐(hydroxymethyl)‐2‐cyclopentenone was isolated in 91 % yield, and similar reactivity was observed for other cyclic enones.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201001612