82111-78-2Relevant academic research and scientific papers
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
One-Pot Tandem Michael Addition/Enantioselective Conia-Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis
Hiramatsu, Rin,Horibe, Takahiro,Ishihara, Kazuaki,Sakakibara, Masato,Takeda, Kazuki
supporting information, p. 16470 - 16474 (2020/07/13)
The first one-pot tandem Michael addition/enantioselective Conia-ene cyclization of N-protected prop-2-yn-1-amines with 2-methylene-3-oxoalkanoates promoted by chiral iron(III)/silver(I) cooperative catalysts has been developed. Alkyl 4-methylenepyrrolidine-3-acyl-3-carboxylates, which can be transformed into β-proline derivatives, are obtained in high yield with high enantioselectivity.
Catalyst-Free Conjugate Addition of Indolizines to in Situ-Generated Oxidized Morita-Baylis-Hillman Adducts
Coelho, Fernando,Silva, Thiago S.,Zeoly, Lucas A.
, p. 5438 - 5448 (2020/05/19)
Sequential one-pot 2-iodoxybenzoic acid (IBX) oxidation of Morita-Baylis-Hillman (MBH) adducts followed by catalyst-free indolizine conjugate addition was developed. The wide scopes of MBH adducts and indolizines were investigated, and densely functionalized adducts were obtained in yields of up to 94%. The conjugate addition step occurred in less than a minute at room temperature with total regioselectivity toward indolizine C3 carbon. Less nucleophilic C1 carbon was also alkylated when C3-substituted indolizines were employed as the substrate.
A Hydrazine Insertion Route to N′-Alkyl Benzohydrazides by an Unexpected Carbon-Carbon Bond Cleavage
Jha, Ajit Kumar,Kumari, Rajkiran,Easwar, Srinivasan
, p. 8191 - 8195 (2019/10/16)
A serendipitous carbon-carbon bond cleavage in the reaction of benzoyl acrylates, derived from Morita-Baylis-Hillman adducts, with hydrazines delivered new N′,N′-disubstituted benzohydrazides. The reaction features a regioselective formation of two carbon
Hypervalent iodine catalysis for selective oxidation of Baylis-Hillman adducts via in situ generation of o-iodoxybenzoic acid (IBX) from 2-iodosobenzoic acid (IBA) in the presence of oxone
Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Rao, Vaidya Jayathirtha
supporting information, p. 10300 - 10304 (2016/12/07)
An efficient, environmentally benign, eco-friendly protocol for selective oxidation of primary and secondary Baylis-Hillman alcohols to the corresponding carbonyl compounds has been developed. We have demonstrated the catalytic use of o-iodoxybenzoic acid
Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)
Barcelos, Rosimeire C.,Zeoly, Lucas A.,Rodrigues, Manoel T.,Ferreira, Bruno R. V.,Eberlin, Marcos N.,Coelho, Fernando
, p. 1557 - 1570 (2015/02/19)
Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo
Regio-and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix
Chaves, Michel R.B.,Moran, Paulo J.S.,Rodrigues, J. Augusto R.
, p. 73 - 77 (2013/11/19)
Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita-Baylis-Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b-c. Employing Amberlite XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a-c and anti-4a-c were isolated in 60-70% yield, with high stereoselectivity (98-99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions.
Noncovalent organocatalytic synthesis of enantioenriched terminal aziridines with a quaternary stereogenic center
De Fusco, Claudia,Fuoco, Tiziana,Croce, Gianluca,Lattanzi, Alessandra
supporting information; experimental part, p. 4078 - 4081 (2012/09/21)
A high-yielding and enantioselective access to novel N-Boc terminal aziridines, bearing a quaternary stereogenic center, has been developed via an aza-Michael initiated ring-closure (aza-MIRC) reaction of α-acyl acrylates with an N-tosyloxy tert-butyl carbamate catalyzed by a chiral amino thiourea. The feasibility of the aziridine regioselective ring-opening to valuable α,α-disubstituted α-amino acid esters has been demonstrated.
Highly enantioselective epoxidation catalyzed by cinchona thioureas: Synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center
Russo, Alessio,Galdi, Gerardina,Croce, Gianluca,Lattanzi, Alessandra
supporting information; experimental part, p. 6152 - 6157 (2012/06/30)
A brilliant debut! Cinchona thioureas have been reported for the first time as catalysts in the area of asymmetric oxidations. They efficiently promote an unprecedented highly enantioselective epoxidation of deactivated 1,1-disubstituted alkenes to terminal epoxides containing a quaternary stereogenic center (see scheme). Copyright
Nanocrystalline magnesium oxide stabilized palladium(0): An efficient reusable catalyst for room temperature selective aerobic oxidation of alcohols
Layek, Keya,Maheswaran,Arundhathi,Kantam, M. Lakshmi,Bhargava, Suresh K.
supporting information; experimental part, p. 606 - 616 (2011/04/25)
Nanocrystalline magnesium oxide-stabilized palladium(0) [NAP-Mg-Pd(0)], as an efficient catalytic system has been employed for the selective oxidation of alcohols using atmospheric oxygen as a green oxidant at room temperature. Various alcohols could be transformed into their corresponding aldehydes or ketones in good to excellent yields using a set of optimal conditions. NanoActive Magnesium Oxide Plus, [NAP-MgO] with its three-dimensional structure and well-defined shape acts as an excellent support for well dispersed palladium(0) nanoparticles. This catalyst can be recovered and reused for several cycles without any significant loss of catalytic activity.
