94348-65-9Relevant academic research and scientific papers
Acceleration of the Morita-Baylis-Hillman reaction by a simple mixed catalyst system
Bugarin, Alejandro,Connell, Brian T.
supporting information; experimental part, p. 4638 - 4641 (2009/09/08)
(Chemical Equation Presented) By using a catalytic amount of 4-dimethylaminopyridine (DMAP) as a nucleophile in the presence of an equal amount of tetramethylethylenediamine (TMEDA) and MgI2, Morita-Baylis-Hillman adducts can be obtained in good to excellent yields from various aromatic and aliphatic aldehydes and cyclic enones/enoates at room temperature after convenient reaction times.
Efficient Baylis-Hillman reactions of cyclic enones in methanol as catalyzed by methoxide anion
Luo, Sanzhong,Mi, Xueling,Xu, Hui,Wang, Peng George,Cheng, Jin-Pei
, p. 8413 - 8422 (2007/10/03)
The Baylis-Hillman reactions of cyclic enones with a variety of aldehydes were investigated. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was found to be a viable catalyst in promoting the reactions of sterically retarded substrates in methanol. The reactions showed clear solvent dependence and only occurred in hydroxylic solvents, especially in methanol. Further consideration on the steric character of DBU and its high basicity jointly with other experimental observations suggests that the methoxide anion should be the "true" Baylis-Hillman catalyst. This has been confirmed by the effectiveness of similar reactions directly employing methoxide as the catalyst. The reaction pathways of this type of catalysis are proposed to depend on the choice of substrates. Supporting experimental observations were demonstrated and discussed in relation to mechanistic considerations. This study also reveals that both DBU and sodium methoxide can be successfully applied as effective catalysts in methanol to promote the Baylis-Hillman reactions for a range of cyclic enones including cyclopent-2-enones, cyclohex-2-enones, γ-pyrone, and 1-benzopyran-4(4H)- ones.
Tandem Conjugate Addition-Aldol Reactions Employing 9-(Phenylseleno)-9-borabicyclononane: A Novel Method for Effecting Formal Aldol Condensations at the α-Carbon of α,β-Unsaturated Ketones
Leonard, William R.,Livinghouse, Tom
, p. 730 - 732 (2007/10/02)
The title compound has been shown to undergo conjugate addition to a variety of α,β-unsaturated ketones to afford β-seleno boron enolates which are convertable to unsaturated ketols upon treatment with aldehydes and subsequent oxidative elimination.
