Article
Chemistry, Multidisciplinary
Fuhao Zhang, Xuan Dai, Lei Dai, Wenrui Zheng, Wai-Lun Chan, Xiaodong Tang, Xumu Zhang, Yixin Lu
Summary: A phosphine-catalyzed highly enantioselective and diastereoselective (3+2) annulation reaction has been developed, allowing convenient access to a range of highly functionalized chiral pyrrolidines. This method utilizes vinylcyclopropanes as a synthon for phosphine-mediated asymmetric annulation, offering new opportunities for the application of cyclopropanes substrates in phosphine-catalyzed organic transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jeremy T. Maddigan-Wyatt, Mitchell T. Blyth, Jhi Ametovski, Michelle L. Coote, Joel F. Hooper, David W. Lupton
Summary: A phosphine-catalyzed approach to pyrrolines has been developed, involving two mechanistically unlinked catalytic processes, and successfully synthesizing various pyrrolines. The reaction shows high sensitivity to the selection of catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Dongqiu Li, Xiaoqian Zhang, Wendan Han, Jiao Jiao, Yuhai Tang, Silong Xu
Summary: This study presents a Lewis base-catalyzed annulation reaction using hepta-2,3,5-trienedioates as substrates. Mild conditions allow for the construction of exocyclic olefinic cyclopentenes through a [3+2] annulation with electron-deficient alkenes, obtaining good yields and moderate E:Z ratios. This reaction involves a tandem [3+2] cyclization and double bond migration, with the ε-ester playing a crucial role in both processes. Additionally, it demonstrates a substrate-controlled divergent reactivity compared to a previous report.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yangyang Wang, Xiaoming Huang, Haojie Ji, Hongwei Zhou, Hongjie Gao, Jianfeng Xu
Summary: A quinine-derived thiourea-promoted enantioselective aza-Friedel-Crafts reaction of 3-aminobenzofurans with isatin-derived ketimines was developed, providing a variety of 3-benzofuran-3-amino-2-oxindoles bearing a quaternary stereocenter with good to excellent yields and moderate to excellent enantioselectivities. The synthetic potential of this concise and efficient protocol was demonstrated by gram-scale preparation and further transformation of the adduct to an optically pure spirocyclic oxindole.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianning Liao, Jipan Dong, Jiaqing Xu, Wei Wang, Yongjun Wu, Yuxia Hou, Hongchao Guo
Summary: A phosphine-catalyzed [3 + 2] annulation reaction has been developed in this study to synthesize multifunctional isoxazoles with moderate to good yields and diastereoselectivities. The use of a spirocyclic chiral phosphine catalyst resulted in up to 89% ee.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ting Wang, Yong You, Zhen-Hua Wang, Jian-Qiang Zhao, Yan-Ping Zhang, Jun-Qing Yin, Ming-Qiang Zhou, Bao-Dong Cui, Wei-Cheng Yuan
Summary: A copper-catalyzed decar-boxylative [3 + 2] cyclization reaction between alkyne-substituted cyclic carbamates and azlactones has been developed, providing optically pure gamma-butyrolactams bearing two adjacent tetrasubstituted carbon stereocenters in high yields with excellent stereo-selectivities (up to 99% yield, 99:1 dr, and 99% ee). This represents the first successful asymmetric synthesis of gamma-butyrolactams containing sterically congested adjacent tetrasubstituted stereocenters via a decarboxylative cyclization pathway.
Article
Chemistry, Applied
Pei-Hao Dou, Yan Chen, Yong You, Zhen-Hua Wang, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: An organocatalyzed asymmetric dearomative [3+2] annulation reaction of electron-deficient 2-nitrobenzo heteroarenes with 3-isothiocyanato oxindoles was developed, providing access to structurally diverse polycyclic spirooxindoles with three contiguous stereogenic centers in high yields with good diastereo- and enantioselectivities. This organocatalysis protocol offers complementary diastereoselectivity compared to previous work with transition metal catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Wen-Xuan Lin, Zhuolin Pei, Cunxi Gong, Huilin Mo, Kai Yang, Ling-Bo Qu, Donghui Wei, Jin-Shuai Song, Shi-Jun Li, Yu Lan
Summary: In the study of the mechanism of phosphine-catalyzed [8+2] cycloaddition, it was found that electrophilicity plays a role in hindering nucleophilic attack but is not predictive of priority.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Xing-Yu Wang, Xiao-Bing Wang, Yin Tian, Cheng Peng, Ming-Sheng Xie, Hai-Ming Guo
Summary: A highly enantioselective dearomative [3 + 2] annulation reaction was achieved using quinolines, isoquinolines, and pyridines with donor-acceptor aminocyclopropanes. By utilizing a C-1-symmetric imidazoline-pyrroloimidazolone pyridine as the tridentate ligand and Co(OTf)2 as the Lewis acid, chiral indolizidine and benzo-fused indolizidine derivatives were obtained with good yields (up to 98%), excellent diastereoselectivities (>20:1 dr), and excellent enantioselectivities (up to 98% ee). Mechanistic experiments and DFT calculations revealed that the tridentate nitrogen ligand acted as a bifunctional chiral ligand, coordinating with the Co(II) salt and forming a H-bond to facilitate the nucleophilic attack of N-heteroaromatics and achieve high enantioselectivity.
Article
Chemistry, Organic
Ramesh A. Gaikwad, Amol T. Savekar, Suresh B. Waghmode
Summary: A facile one-pot metal-free, base-mediated formal [3 + 2] and [4+ 2] dearomative ipso-cycloaddition of para-quinone methides (p-QMs) with halo alcohols has been designed for the efficient construction of 2-oxa-spirocyclohexadienones in excellent yield under mild reaction conditions. The commercial availability of the bases, reagents, and convenient reaction procedure makes it an attractive method for ipso-cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huamin Wang, Yibo Wei, Yuqiang Li, Shuangshuang Long, Li-Juan Sun, Shixiong Li, Ying-Wu Lin
Summary: A new strategy for the enantioselective synthesis of axially chiral N-aryl succinimides was developed using [3 + 2] annulation of MBH carbonates and N-aryl maleimides under chiral phosphine. This process allows for the efficient construction of stereogenic carbon centers and remote C-Ar-N atropisomeric chirality. The method exhibits mild reaction conditions, high efficiency, scalability, and a broad substrate scope.
Article
Chemistry, Multidisciplinary
Chuan Xiang Alvin Tan, Rui Li, Fuhao Zhang, Lei Dai, Nisar Ullah, Yixin Lu
Summary: A sequential phosphine-catalyzed asymmetric [3+2] annulation of aldimines has been developed, utilizing an oxidative central-to-axial chirality transfer strategy. This approach is operationally simple and allows for the rapid synthesis of highly enantioselective 2-arylpyrroles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Min Liu, Jianning Liao, Yujie Dong, Wangyu Shi, Yimin Hu, Jiaqing Xu, Wei Wang, Yong Xu, Hongchao Guo
Summary: The acidic hydrogen-tethered allylic carbonates were successfully applied in phosphine catalysis, showing high yields in (4+2) annulation reactions with sulfamate-derived cyclic imines. A moderate ee was obtained, and the zwitterionic intermediate acted as a four-membered synthon.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Lu-Wen Zhang, Li Wang, Nan Ji, Si-Yang Dai, Wei He
Summary: The method utilizes TBHP as an oxidant to determine reaction rate, with chiral amine-thiourea catalyst effectively controlling stereoselectivity and KOH promoting deprotonation. 22 examples of α,β-unsaturated ketones with various substituent groups are smoothly converted into α-carbonyl epoxides with moderate to excellent enantiomeric excess.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
David Guzman Rios, Miguel A. Romero, Jose A. Gonzalez-Delgado, Jesus F. Arteaga, Uwe Pischel
Summary: The [Ru(bpy)2(Nor)2]2+ complex is an efficient catalyst for the aldol reaction of acetone with activated benzaldehydes in a buffered aqueous solution. The role of the metal as an activator for nornicotine organocatalyst ligands enhances catalytic activity by about 4.5 times compared to free nornicotine. The study provides insights into the synergistic effect of organic catalysts and metals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Khanh-Duy Huynh, Houssein Ibrahim, Lucie Bouchardy, Chloee Bournaud, Emilie Kolodziej, Martial Toffano, Giang Vo-Thanh
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Thi-Thuy-Duong Ngo, Kenta Kishi, Makoto Sako, Masashi Shigenobu, Chloee Bournaud, Martial Toffano, Regis Guillot, Jean-Pierre Baltaze, Shinobu Takizawa, Hiroaki Sasai, Giang Vo-Thanh
Article
Chemistry, Multidisciplinary
Samia Guezane-Lakoud, Martial Toffano, Louisa Aribi-Zouioueche
HETEROATOM CHEMISTRY
(2017)
Article
Chemistry, Organic
Anne-Laure Barthelemy, Alexis Prieto, Patrick Diter, Jerome Hannedouche, Martial Toffano, Elsa Anselmi, Emmanuel Magnier
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Lucie Bouchardy, Violeta Rodriguez-Ruiz, Chloee Bournaud, Francois-Didier Boyer, Martial Toffano, Patrick Judeinstein, Giang Vo-Thanh
Article
Chemistry, Applied
Alexis Prieto, Patrick Diter, Martial Toffano, Jerome Hannedouche, Emmanuel Magnier
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Multidisciplinary
Samia Guezane Lakoud, Rim Aissa, Regis Guillot, Martial Toffano, Louisa Aribi-Zouioueche
Article
Chemistry, Physical
Samra Razi, Saoussen Zeror, Mounia Merabet-Khelassi, Emilie Kolodziej, Martial Toffano, Louisa Aribi-Zouioueche
Summary: This study compares two reaction approaches for the efficient enantioselective cleavage of alpha-phenyl ethyl esters, finding high efficiency in the presence of sodium carbonates and strong influence of acyl-chain length on conversion rates in micro-aqueous media. Lipase CAL-B demonstrates high enantioselectivities towards (R)-1-phenyl ethanol enantiomer in both conditions but with reactivity modulated by acyl-chain properties.
Article
Chemistry, Physical
Zhiwei Jiang, Martial Toffano, Giang Vo-Thanh, Chloee Bournaud
Summary: An efficient and flexible synthesis of a new class of chiral bifunctional NHC catalyst has been reported, which promotes highly diastereoselective trans-cyclopentannulation of enals and enones with good yields and excellent enantioselectivity. This methodology could be applied to a large variety of substrates.
Article
Chemistry, Multidisciplinary
Stephane Wittmann, Thomas Martzel, Cong Thanh Pham Truong, Martial Toffano, Sylvain Oudeyer, Regis Guillot, Chloee Bournaud, Vincent Gandon, Jean-Francois Briere, Giang Vo-Thanh
Summary: Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Rim Aissa, Samia Guezane-Lakoud, Martial Toffano, Lynda Gali, Louisa Aribi-Zouioueche
Summary: The chiral organocatalyst Fiaud's acid is effective in synthesizing bis alpha-aminophosphonates with excellent antifungal properties, particularly compounds 4a, 4b, 4e, 4h, 4k, and 4l exhibit strong fungicidal activity against Fusarium oxysporum and Botrytis cinerea. These compounds also demonstrate antioxidant and anti-tyrosinase abilities.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Louisa Aribi-Zouioueche, Mounia Merabet-Khelassi, Nabila Braia, Martial Toffano
Summary: In this study, enantiomerically pure forms of several compounds were prepared through enzymatic kinetic resolution in organic media. The resulting compounds exhibited high enantiopurity and good synthesis yields.
BIOCATALYSIS AND BIOTRANSFORMATION
(2023)
Review
Chemistry, Multidisciplinary
Thi Thuy Duong Ngo, Khanh Duy Huynh, Houssein Ibrahim, Thi Huong Nguyen, Chloee Bournaud, Martial Toffano, Giang Vo-Thanh
VIETNAM JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Rim Aissa, Samia Guezane-Lakoud, Emilie Kolodziej, Martial Toffano, Louisa Aribi-Zouioueche
NEW JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
