Article
Chemistry, Organic
Faqian He, Jiawen Wang, Fang Zhou, Houchao Tao, Xiaoyu Yang
Summary: The direct regio- and enantioselective amination of acyclic branched alpha-alkynyl ketones with azodicarboxylates has been achieved through chiral phosphoric acid catalysis, yielding alpha-hydrazido-alpha-alkynyl ketone products with high enantioselectivity. Control experiments showed the importance of the alkynyl group in the ketone substrate for both reactivity and stereoselectivity, and facile derivatizations of the chiral product highlight the value of this approach in asymmetric synthesis of alpha-tertiary amines and N-containing heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Tong Lv, Jinhui Feng, Xi Chen, Yuyang Luo, Qiaqing Wu, Dunming Zhu, Yanhe Ma
Summary: Mutant amine dehydrogenases (LsAmDHs) were developed through directed evolution from L-phenylalanine dehydrogenase, enabling the asymmetric reductive amination of 2,2-disubstituted-1,3-cyclopentadiones with high yield. This study not only synthesized the corresponding stereoisomeric fi-amino ketones, but also provided a useful tool for addressing the challenges in asymmetric reductive amination of diketones.
Article
Chemistry, Organic
Sigrid A. Kiledal, Roxane Jourdain, Sreekumar Vellalath, Daniel Romo
Summary: An enantioselective three-component reaction was developed for the synthesis of tetrahydropyridazinones, delivering optically active products with unexpected rearrangements explored. The use of allyl methyl malonate introduced a second stereocenter during subsequent transformations.
Article
Chemistry, Organic
Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou
Summary: A new synthetic method for the selective transfer hydrogenation of nitriles to primary amine-boranes and secondary amines has been developed. The method demonstrates high selectivity and yields up to 95%, and has been successfully applied in the synthesis of N-15 labeled compounds with an 89% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiao-kang Nie, Yue Chen, Shi-qi Zhang, Xin Cui, Zhuo Tang, Guang-xun Li
Summary: We have developed a catalytic asymmetric tandem reaction for the synthesis of chiral alpha-amino ketones, by mimicking the catalytic mechanism of glucosamine-6-phosphate synthase in organisms.
Article
Chemistry, Multidisciplinary
Alessandra Lattanzi
Summary: The development of organocatalysis and the use of Michael addition reaction have greatly contributed to the synthesis of quaternary stereocenters and the preparation of functionalized building blocks. In this account, the authors highlight their achievements in accessing novel heterocycles with quaternary stereocenters, particularly focusing on the use of organocatalysis derived from Cinchona alkaloids. The enantioenriched heterocycles obtained were further manipulated to prepare useful compounds for downstream applications.
Review
Biochemistry & Molecular Biology
Silvia Vera, Aitor Landa, Antonia Mielgo, Inaki Ganboa, Mikel Oiarbide, Vadim Soloshonok
Summary: Aldehydes are widely used in organic synthesis, and the enantioselective alpha-functionalization of aldehydes has attracted great interest. Alpha-branched aldehydes are particularly challenging substrates due to reactivity and selectivity issues. However, in the past 15 years, several catalytic approaches have been discovered that exhibit good yields and selectivities in the alpha-functionalization of alpha-branched aldehydes.
Article
Chemistry, Organic
Yanfang Han, Long Zhang, Sanzhong Luo
Summary: A highly diastereo- and enantioselective retro-Claisen reaction has been developed using chiral primary amine catalysis. This reaction enables efficient synthesis of chiral beta,beta-diaryl-alpha-branched ketones with excellent stereoselectivities. The reaction proceeds through a tandem sequence involving benzylic C-C bond formation, C-C bond cleavage, and stereospecific enamine protonation. The use of o-quinone methides as diaryl precursors allows for a broad substrate scope, mild reaction conditions, and a high degree of stereocontrol.
Article
Chemistry, Organic
Francesca Franco, Sara Meninno, Jacob Overgaard, Sergio Rossi, Maurizio Benaglia, Alessandra Lattanzi
Summary: An enantioselective synthesis method for functionalized triflones with a quaternary stereocenter has been developed, utilizing the Michael reaction and nucleophilic acyl substitution. The study highlights the potential of the triflinate anion as a leaving group for stereocontrolled postfunctionalizations.
Article
Chemistry, Applied
Khadidja Bourahla, Yahia Lemmouchi, Charafeddine Jama, Christian Rolando, Ahmed Mazzah
Summary: The aim of this study was to investigate the adsorption mechanism of branched polyethyleneimine (bPEI) onto cellulose acetate (CA) fibers and evaluate its impact on adsorption of aldehydes and shelf life.
REACTIVE & FUNCTIONAL POLYMERS
(2022)
Article
Chemistry, Multidisciplinary
Matteo Balletti, Tommy Wachsmuth, Antonio Di Sabato, Will C. Hartley, Paolo Melchiorre
Summary: Here, a photochemical organocatalytic method for asymmetric introduction of perfluoroalkyl fragments at the gamma-position of alpha-branched enals is reported. The method utilizes the ability of extended enamines to form photoactive electron donor-acceptor complexes with perfluoroalkyl iodides, generating radicals through an electron transfer mechanism under blue light irradiation. The use of a chiral organocatalyst derived from cis-4-hydroxy-l-proline ensures high stereocontrol and complete site selectivity for the more distal gamma position of the dienamines.
Article
Chemistry, Organic
Sayan Shee, Deeptanu Sarkar, Akkattu T. Biju
Summary: The enantioselective synthesis of functionalized pyrazoloquinolin-3-ones via N-heterocyclic carbene-catalyzed cascade reaction of alpha-bromoenals with 2-aminoaryl N-tosyl hydrazones is described. The in situ-generated alpha,beta-unsaturated acylazoliums undergo an aza-Michael-Mannich-lactamization sequence to afford tricyclic products with three contiguous stereocenters, including a sterically demanding quaternary stereocenter with high enantioselectivity. The preference for the unprotected amine-triggered aza-Michael pathway over the competing amidation pathway is notable.
Article
Chemistry, Physical
Dekun Zhang, Ying-Bo Shao, Wansen Xie, Yunrong Chen, Wei Liu, Hanyang Bao, Faqian He, Xiao-Song Xue, Xiaoyu Yang
Summary: In this paper, a remote enantioselective desymmetrization protocol for asymmetric aromatic aminations of 9,10-dihydroacridines is disclosed. A new spirocyclic chiral phosphoric acid (CPA) catalyst is used to achieve this synthesis, leading to a wide range of chiral dihydroacridines with excellent enantioselectivities. This method is also applicable in the construction of stereogenic silicon center and kinetic resolution of unsymmetrical dihydroacridine derivatives. Density functional theory calculations elucidate the origin of the reactions' excellent regio- and enantioselectivity.
Article
Chemistry, Organic
Wenliang Zhang, Yujing Yao, Yaling Xu, Xueying Zhou, Ge Wu
Summary: The study reveals a new utilization of amine hydrochloride as a bifunctional reagent, demonstrated through copper-catalyzed aminochlorination of maleimides. The prominent features include a simple and efficient catalyst system, broad substrate scope, readily scalable reaction, and late-stage modification of small-molecule drugs.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Teng Liu, Shaofei Ni, Wusheng Guo
Summary: We have reported the first amine nucleophilic approach for the modular construction of enantioenriched protected alpha-quaternary amino acids. The use of an alcohol solvent in this method stabilizes the COOMe-bonded Cu-allenylidene electrophilic intermediate, allowing it to couple with amine nucleophiles before decomposition. This reaction has high enantioselectivity and is compatible with a wide range of functional groups. The resulting protected alpha-amino acids can be easily converted into various precious enantioenriched amines featuring alpha-hindered tertiary carbon centers.
Article
Chemistry, Applied
Loic Pantaine, Francois Richard, Jerome Marrot, Xavier Moreau, Vincent Coeffard, Christine Greck
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Organic
Loic Pantaine, Aragorn Laverny, Xavier Moreau, Vincent Coeffard, Christine Greck
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Organic
Christina Despotopoulou, Sean C. McKeon, Robert Connon, Vincent Coeffard, Helge Mueller-Bunz, Patrick J. Guiry
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Inorganic & Nuclear
Mouhamad Awada, Sebastien Floquet, Jerome Marrot, Mohamed Haouas, Sara P. Morcillo, Christophe Bour, Vincent Gandon, Vincent Coeffard, Christine Greck, Emmanuel Cadot
JOURNAL OF CLUSTER SCIENCE
(2017)
Article
Chemistry, Multidisciplinary
Maxime Giardinetti, Jerome Marrot, Vincent Coeffard, Xavier Moreau, Christine Greck
NEW JOURNAL OF CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Audrey Mauger, Jonathan Farjon, Pierrick Nun, Vincent Coeffard
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Maxime Giardinetti, Jerome Marrot, Christine Greck, Xavier Moreau, Vincent Coeffard
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Anne-Sophie Marques, Jerome Marrot, Isabelle Chataigner, Vincent Coeffard, Guillaume Vincent, Xavier Moreau
Article
Chemistry, Multidisciplinary
Anne-Sophie Marques, Thibaut Duhail, Jerome Marrot, Isabelle Chataigner, Vincent Coeffard, Guillaume Vincent, Xavier Moreau
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Jerome Fischer, Lucas Mele, Helene Serier-Brault, Pierrick Nun, Vincent Coeffard
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Environmental Sciences
Ehu C. Aka, Medy C. Nongbe, Tchirioua Ekou, Lynda Ekou, Vincent Coeffard, Francois-Xavier Felpin
JOURNAL OF ENVIRONMENTAL SCIENCES
(2019)
Article
Chemistry, Organic
Jerome Fischer, Helene Serier-Brault, Pierrick Nun, Vincent Coeffard
Review
Chemistry, Organic
Jerome Fischer, Pierrick Nun, Vincent Coeffard
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Multidisciplinary
Louis Peault, Pierrick Nun, Erwan Le Grognec, Vincent Coeffard
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Loic Pantaine, Vincent Humblot, Vincent Coeffard, Anne Vallee
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2017)
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)
