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Efficient Catalysis of Aqueous Morita–Baylis–Hillman Reactions of Cyclic Enones by a Bicyclic Imidazolyl Alcohol (Eur. J. Org. Chem. 35/2012)
Author(s) -
Gomes Juliana C.,
Rodrigues Jr. Manoel T.,
Moyano Albert,
Coelho Fernando
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201290096
Subject(s) - chemistry , bicyclic molecule , bifunctional , catalysis , lewis acids and bases , alcohol , baylis–hillman reaction , brønsted–lowry acid–base theory , organocatalysis , organic chemistry , lewis acid catalysis , combinatorial chemistry , medicinal chemistry , stereochemistry , enantioselective synthesis
The cover picture shows a Morita–Baylis–Hillman reaction between cyclic enones and aldehydes, catalyzed by a bicyclic imidazolyl alcohol and performed in water, the most eco‐friendly solvent. The new bifunctional catalyst presents in its structure two key active centers: one acting as a Lewis base in association with a second one acting as a Brønsted acid. This synergic association seems to stabilize the zwitterionic species involved in the catalytic cycle of this synthetically useful chemical transformation. The new protocol avoids the use of phosphanes and has sustainable features. Details are discussed in the article by F. Coelho et al. on p. 6861 ff.