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Relevant academic research and scientific papers

TiO2@UiO-68-CIL: A Metal-Organic-Framework-Based Bifunctional Composite Catalyst for a One-Pot Sequential Asymmetric Morita-Baylis-Hillman Reaction

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.

Asymmetric Morita–Baylis–Hillman Reaction: Catalyst Development and Mechanistic Insights Based on Mass Spectrometric Back-Reaction Screening

An efficient protocol for the evaluation of catalysts for the asymmetric Morita–Baylis–Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of methyl acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate- and enantioselectivity-determining.

Bifunctional (Thio)urea-Phosphine Organocatalysts Derived from d -Glucose and α-Amino Acids and Their Application to the Enantioselective Morita-Baylis-Hillman Reaction

Novel (thio)urea-tertiary phosphines were developed for use as bifunctional organocatalysts readily available from naturally occurring molecules: saccharides and amino acids. The efficiency of the organocatalysts was demonstrated in the asymmetric Morita-

Enantioselective Morita-Baylis-Hillman reaction organocatalyzed by glucose-based phosphinothiourea

A class of bifunctional phosphinothioureas derived from saccharide was developed as new organocatalysts for the enantioselective Morita-Baylis-Hillman reaction between acrylates and aldehydes. With 10 mol% of glucose-based phosphinothiourea 1d, the allylic alcohols were obtained in up to 96% yield and 83% ee under mild reaction conditions.

Enantioselective Morita-Baylis-Hillman reaction promoted by l-threonine-derived phosphine-thiourea catalysts

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.

A new dual catalytic system for asymmetric morita-baylis-hillman reaction

High yields and enantioselectivities up to 88% were achieved in asymmetric Morita-Baylis-Hillman reactions using a combination of chiral amino acid derived guanidines and triphenylphosphane as a novel dual catalytic system.

Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita-Baylis-Hillman reactions of acrylates with aromatic aldehydes

A new type of chiral bifunctional phosphinothiourea derived from l-valine is synthesized and used as an organocatalyst in the enantioselective Morita-Baylis-Hillman reaction of aromatic aldehydes with acrylates. The desired products were obtained in good