108945-27-3

Upstream product

• 67-56-1 methanol 
• 140630-32-6 3-hydroxy-2-methylene-3-phenylpropanoic acid 
• 100-52-7 benzaldehyde 
• 114106-84-2 (S)-(-)-methyl 3-<2-(hydroxymethyl)pyrrolidine>propanoate 
• 124957-36-4 Methyl 3-acetoxy-2-methylene-3-phenylpropanoate 
• 292638-85-8 acrylic acid methyl ester 
• 2160-89-6 1,1,1,3,3,3-hexafluoroisopropyl acrylate 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 956833-12-8 methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate 
• 170751-34-5 N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide 
• 22731-83-5 S,S-diphenylsulphoximine 
• 100-51-6 benzyl alcohol 
• 97-72-3 2-Methylpropionic anhydride 
• 253197-70-5 1,1,1,3,3,3-hexafluoropropan-2-yl (R)-3-hydroxy-2-methylene-3-phenylpropanoate 

Downstream Products

• 36041-80-2 (2R,3S)-methyl 3-hydroxy-2-methyl-3-phenylpropanoate 
• 76549-03-6 methyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoate 

Relevant academic research and scientific papers

Organocatalytic Asymmetric Allylic Alkylations of Sulfoximines

An enantio- and regioselective allylic alkylation of sulfoximines with Morita-Baylis-Hillman carbonates was developed. The asymmetric reaction is directed by a quinidine-derived organocatalyst providing a range of optically active α-methylene β-sulfoximidoyl esters in high yields (up to 93%) with good to excellent enantiomeric excesses (up to 95%) under mild reaction conditions.

Rhodium-Catalyzed [2+2+2] Cycloadditions of Diynes with Morita-Baylis-Hillman Adducts: A Stereoselective Entry to Densely Functionalized Cyclohexadiene Scaffolds

A rhodium-catalyzed asymmetric synthesis of 5,5-disubstituted cyclohexa-1,3-dienes has been achieved by [2+2+2] cycloaddition reactions between diynes and Morita-Baylis-Hillman (M-B-H) adducts as unsaturated substrates. Products containing two adjacent ch

Synthesis of enantiomerically enriched Baylis-Hillman alcohols from their acetates: Combination of kinetic resolution during the salt formation with (DHQD)2PHAL and following asymmetric induction during hydrolysis with NaHCO3 as a water surrogate

Enantiomerically enriched Baylis-Hillman alcohols 2a-d (S) were prepared in 25-42% yields with optical purities of 54-92% ee by using the combined concept of kinetic resolution during the salt formation of racemic Baylis-Hillman acetates 1a-d with (DHQD)2PHAL and the asymmetric induction during the SN2′ type reaction with sodium bicarbonate as a water surrogate.

Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis

Asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) carbonates with less-nucleophilic phenols mediated by nucleophilic amine catalysis was successfully developed. A variety of substituted aryl allyl ethers were afforded with moderate to high yields with excellent enantioselectivities. The chiral MBH alcohol could be easily accessed from the corresponding aryl allyl ether.

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.

First application of chiral ionic liquids in asymmetric Baylis-Hillman reaction

The first example of the use of chiral ionic liquids as reaction media in the asymmetric Baylis-Hillman reaction was described using N-alkyl-N- methylephedrinium salts. Good yields and significant enantiomeric excesses were obtained. The first example of

A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: Highly enantioselective synthesis of three-dimensional heterocyclic compounds

In this communication, a chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction of unmodified Morita-Baylis-Hillman alcohols with azomethine imines has been achieved through a kinetic resolution of MBH alcohols under mild conditions

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.

Synthetic method of multi-hydrogen-bond ferrocene catalyst

The invention provides a synthetic method of a multi-hydrogen-bond ferrocene catalyst. The optical pure (R)-N,N-dimethyl ferrocene ethylamine as a starting raw material, after the lithiation, a diphenylphosphine group is introduced to perform the acetylat

P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis

The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of methyl acrylate with benzaldehyde derivatives.