85736-12-5Relevant academic research and scientific papers
Stereoelectronic Control of Intramolecular Michael Addition Reactions
Ellis, Graham W. L.,Johnson, C. David,Rogers, David N.
, p. 5090 - 5095 (1983)
Concepts of stereoelectronic control lead to the conclusion that the 5-endo-trig ring closure of (E)-2-methyl-3-oxo-5-phenylpent-4-en-2-ol should be disfavored.However, the acid-catalyzed ring closure in trifluoroacetic acid occurs readily, suggesting an
α′-Hydroxyenones as mechanistic probes and scope-expanding surrogates for α,β-unsaturated aldehydes in N-heterocyclic carbene-catalyzed reactions
Chiang, Pei-Chen,Rommel, Michael,Bode, Jeffrey W.
supporting information; experimental part, p. 8714 - 8718 (2009/10/23)
N-heterocyclic carbene-catalyzed reactions of α,β-unsaturatedaldehydes and a variety of electrophiles allow the facile preparation o f a diverse array of annulation products including trisubstituted cyclopentenes, γ-lactams, and bicyclic β-lactams. The substrate scope of these reactions, however, is limited by the difficulties of preparing the starting α,β-unsaturated aldehydes. We now report that α′- hydroxyenones, which can be prepared in a single convenient step from aromatic and heteroaromatic aldehydes, can serve as efficient surrogates for enals in the annulation reactions. This protocol allows the facile preparation and use of substrates bearing nitrogen heterocycles. These reagents have also allowed us to demonstrate that, in contrast to other classes of aldehydes, the formation of the Breslow intermediate from enals and N-heterocyclic carbenes is irreversible under the reaction conditions.
A Novel and Practical Synthetic Method of 3(2H)-Furanone Derivatives
Sakai, Takashi,Yamawaki, Akitoshi,Ito, Hiroshi,Utaka, Masanori,Takeda, Akira
, p. 1199 - 1201 (2007/10/02)
A novel convenient synthetic method of 5-aryl-2,2-dimethyl-3(2H)-furanones (aryl = C6H5, 2-CH3C6H4, 3-CH3C6H4, 4-CH3C6H4, 2-ClC6H4, 4-ClC6H4, 2,4-Cl2C6H3) is described.It involves the Claisen-Schmidt condensation (potassium hydroxide/ethanol) of aromatic
