1341212-16-5Relevant articles and documents
TiO2@UiO-68-CIL: A Metal-Organic-Framework-Based Bifunctional Composite Catalyst for a One-Pot Sequential Asymmetric Morita-Baylis-Hillman Reaction
Hu, Yu-Hong,Liu, Cong-Xue,Wang, Jian-Cheng,Ren, Xiu-Hui,Kan, Xuan,Dong, Yu-Bin
, p. 4722 - 4730 (2019)
A chiral ionic liquid (CIL) moiety of a l-pyrrolidin-2-ylimidazole-decorated homochiral UiO-68-type metal-organic framework, UiO-68-CIL (1), was successfully prepared by the combination of a new premodified chiral CIL ligand (H2L-CIL) and ZrCl4 via a solvothermal method. The TiO2-loaded TiO2@UiO-68-CIL (2) was prepared by impregnating 1 in a toluene solution of Ti(OPri)4 and sequential in situ hydrolysis. The obtained 2 can be a bifunctional asymmetric heterogeneous catalyst to successfully promote the one-pot Morita-Baylis-Hillman reaction starting from aromatic alcohols in a tandem way.
Enantioselective Morita-Baylis-Hillman reaction promoted by l-threonine-derived phosphine-thiourea catalysts
Han, Xiaoyu,Wang, Youqing,Zhong, Fangrui,Lu, Yixin
supporting information; experimental part, p. 6734 - 6740 (2011/11/05)
A series of bifunctional phosphine-thiourea organic catalysts based on natural amino acid scaffolds were designed and prepared. l-Threonine-derived bifunctional phosphine catalysts were found to be very efficient in promoting asymmetric Morita-Baylis-Hillman (MBH) reaction of acrylates with aromatic aldehydes, affording the desired MBH adducts with up to 90% ee. To gain mechanistic insights into the reaction, the effects of adding various additives on the MBH reaction were investigated. We propose that the hydrogen bonding interactions between the thiourea moiety of the catalyst and the enolate intermediate are crucial for the stereochemical outcome of the reaction. The method described in this report may provide a practical solution to the enantioselective MBH reaction of simple acrylates.