73255-39-7Relevant academic research and scientific papers
Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines
Booker-Milburn, Kevin I.,Knowles, Jonathan P.,Latter, Francesca,Schwarz, Maria,Steeds, Hannah G.
supporting information, p. 4986 - 4990 (2021/07/19)
The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji-Trost sequence leading to a surprisingly facile intramolecular Diels-Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.
Facile synthesis of biarylmethanes and tetrasubstituted arenes: Via a base-mediated [3 + 3] benzannulation reaction of Morita-Baylis-Hillman adducts and unsaturated sulfones
Yadav, Deepak,Sharma, Sunil K.,Menon, Rajeev S.
, p. 4073 - 4076 (2019/04/30)
A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita-Baylis-Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products
Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction
Pereira, Mathias Prado,Souza Martins, Rafaela De,De Oliveira, Marcone Augusto Leal,Bombonato, Fernanda Irene
, p. 23903 - 23913 (2018/07/13)
In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-Baylis-Hillman (MBH) reaction. The ionic liquids derivative from l-proline and l-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from l-valine, l-leucine, and l-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.
Decarboxylative Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbamates
Do?ekal, Vojtěch,?imek, Michal,Dra?ínsky, Martin,Vesely, Jan
supporting information, p. 13441 - 13445 (2018/09/21)
The present study reports the organocatalytic enantioselective allylic amination of Morita–Baylis–Hillman carbamates efficiently catalyzed by a chiral amine in the presence of a Br?nsted acid. Chiral allylic amines were produced in high yields (up to 98 %) and enantioselectivities (up to 97 % ee). This method provides an efficient and easily performed route to prepare α-methylene-β-lactams, and other optically active β-lactams, such as the cholesterol-lowering drug Ezetimibe.
A cascade synthesis of: S -allyl benzoylcarbamothioates via Mumm-type rearrangement
Dahiya, Anjali,Ali, Wajid,Alam, Tipu,Patel, Bhisma K.
supporting information, p. 7787 - 7791 (2018/11/21)
A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in
Copper-Catalyzed Asymmetric 1,2-Addition of Grignard Reagents to 3-Acyl 2 H -chromenes
Calvo, Beatriz C.,Minnaard, Adriaan J.
, p. 2624 - 2628 (2017/10/06)
Enones in which the carbon-carbon double bond is part of the pharmacologically important 2 H -chromene (2 H -1-benzopyran) nucleus undergo asymmetric copper-catalyzed 1,2-addition of Grignard reagents. High yields and enantiomeric excesses up to 84% are o
Proline-Mediated Baylis-Hillman Reaction of Methyl Vinyl Ketone without a Co-catalyst under Solvent-Free Conditions
Inani, Heena,Jha, Ajit Kumar,Easwar, Srinivasan
, p. 128 - 132 (2016/12/26)
A proline-mediated Baylis-Hillman reaction of methyl vinyl ketone with aromatic aldehydes has been carried out without using any co-catalyst, under solvent-free conditions. The reaction works efficiently at 60 °C in the presence of a small amount of water
A 2D Coordination Network That Detects Nitro Explosives in Water, Catalyzes Baylis-Hillman Reactions, and Undergoes Unusual 2D→3D Single-Crystal to Single-Crystal Transformation
Sharma, Vivekanand,De, Dinesh,Pal, Sanchari,Saha, Prithwidip,Bharadwaj, Parimal K.
supporting information, p. 8847 - 8855 (2017/08/14)
The solvothermal reaction of Zn(NO3)2·6H2O and a linear dicarboxylate ligand H2L, in the presence of urotropine in N,N′-dimethylformamide (DMF), gives rise to a new porous two-dimensional (2D) coordination netwo
Control of Chemo-, Regio-, and Enantioselectivity in Copper Hydride Reductions of Morita-Baylis-Hillman Adducts
Linstadt, Roscoe T. H.,Peterson, Carl. A.,Jette, Carina I.,Boskovic, Zarko V.,Lipshutz, Bruce H.
supporting information, p. 328 - 331 (2017/04/21)
Nonracemically ligated copper hydride can be used to effect tandem SN2′/1,2-reductions of racemic Morita-Baylis-Hillman (MBH) acetates to access enantioenriched chiral allylic alcohols with defined olefin geometry. MBH esters, including those w
A Porous Cu(II)-MOF with Proline Embellished Cavity: Cooperative Catalysis for the Baylis-Hillman Reaction
De, Dinesh,Pal, Tapan K.,Bharadwaj, Parimal K.
supporting information, p. 6842 - 6844 (2016/07/27)
l-Proline has been covalently attached in a rigid linear ligand, H4L, having an isophthalate moiety at each terminal to form the chiral ligand, H4LPRO. This linker has been used for the construction of a porous MOF, LCuPRO
