Article
Chemistry, Organic
Alberto Llobat, Jorge Escorihuela, Santos Fustero, Mercedes Medio-Simon
Summary: In this study, homopropargyl amines and chiral homoallenyl amines were successfully synthesized by the addition of propargylmagnesium bromide to fluorinated aromatic sulfinyl imines. The choice of coordinating or noncoordinating solvents was found to have a significant impact on the diastereoselectivity outcomes. DFT calculations were used to rationalize the regio- and diastereoselectivities observed experimentally.
Article
Chemistry, Organic
Ziyi Li, Nana Wang, Jiang Liu, Haibo Mei, Vadim A. Soloshonok, Jianlin Han
Summary: A new reactivity mode of tert-butanesulfinamide has been developed for rapid assembly of poly functionalized isothiazoles through C-S and O-S bond cleavage of N-propargyl tert-butanesulfinylamide. This intramolecular cyclization reaction is conducted under mild conditions and tolerates several fluoroalkyl and substituted phenyl groups with good chemical yields, providing an easy strategy for the synthesis of isothiazoles.
Article
Chemistry, Organic
Michael J. Kerner, Christian A. Kuttruff, Maxim Chevliakov, Frederic G. Buono, Donghong A. Gao, Mariusz Krawiec, Carl A. Busacca, Chris H. Senanayake, Peter Wipf, Jonathan T. Reeves
Summary: The addition of carbamoyl anions to azirines provides synthetically useful 2-aziridinyl amide building blocks with high diastereoselectivity. The method was successfully employed for incorporating an aziridine residue into a dipeptide segment.
Article
Chemistry, Organic
Hsien-Liang Cho, Chien-Chen Lai, Yi-Hung Liu, Hsiu-Fu Hsu, Shie-Ming Peng, Sheng-Hsien Chiu
Summary: This paper reports the insertion of Pd(II) into an initially achiral rotaxane, resulting in two chiral metallorotaxanes. Chiral additives and chiral TRISPHAT counteranions were used to confirm the existence of chirality and resolve the enantiomers of the C-2-symmetrical N-heterocyclic carbene complex.
Article
Chemistry, Multidisciplinary
Saikat Das, Azusa Kondoh, Masahiro Terada
Summary: The direct use of cyanohydrin ether derivatives as less acidic pronucleophiles was achieved for the first time in the catalytic enantioselective Michael addition reaction under transition metal free conditions. Chiral bis(guanidino)iminophosphoranes as the higher order organosuperbase facilitated the intended catalytic Michael addition to enones, giving rise to the corresponding products in high yields with moderate to high diastereo- and enantioselectivities in most cases. Further elaboration of the corresponding enantioenriched product was conducted by derivatization into a lactam derivative through hydrolysis followed by cyclo-condensation.
Article
Chemistry, Organic
David A. Gutierrez, James Fettinger, K. N. Houk, Kaori Ando, Jared T. Shaw
Summary: This study describes the Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral alpha-alkoxy N-tosyl imines with stereochemical control, resulting in the synthesis of two isomers of clausenamide.
Review
Chemistry, Applied
Ilya N. Egorov, Sougata Santra, Grigory Zyryanov, Adinath Majee, Alakananda Hajra, Oleg N. Chupakhin
Summary: This review focuses on the asymmetric addition reactions of non-carbon nucleophiles to imines. Chiral catalysts are used to achieve control over the stereochemistry of the addition reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xiao Jin, Vijay K. Chatare, Po-Cheng Yu, Michael R. Gau, Owen T. O'Sullivan, Rodrigo B. Andrade
Summary: The DMM reaction is a method for synthesizing chiral 2-amino cyclohexenes that proceeds at low temperature while maintaining stereochemical fidelity. The product yields range from 55-82%, with diastereomeric ratios as high as >19:1.
Article
Chemistry, Physical
Daisuke Sakamoto, Isabel Gay Sanchez, Jiri Rybacek, Jaroslav Vacek, Lucie Bednarova, Marketa Pazderkova, Radek Pohl, Ivana Cisarova, Irena G. Stara, Ivo Stary
Summary: This study describes an asymmetric synthesis method for the preparation of optically pure and conformationally locked oxabenzo[5]helicenes. These compounds can be transformed into cycloiridated organometallics and exhibit excellent catalytic performance in asymmetric transfer hydrogenation reactions.
Article
Chemistry, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
Article
Chemistry, Organic
Francisco Foubelo, Carmen Najera, Jose M. Sansano, Miguel Yus
Summary: Transition metal-catalyzed reactions of N-sulfinyl imines lead to chiral amines with high yields and diastereo- or enantioselectivities. Metals such as titanium, copper, ruthenium, rhodium, palladium, and silver have been successfully used as catalysts in various carbon-carbon forming reactions and hydrogenation reactions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Tushar Janardan Pawar, Liliette Barcelona-Cazanave, Israel Bonilla-Landa, Magdalena Escobar, J. Oscar C. Jimenez-Halla, Alma Altuzar-Molina, Patricia Romero-Arellano, Andrew J. F. Edmunds, Martin Aluja, Jose Luis Olivares-Romero
Summary: This study presents a highly efficient iridium-catalyzed asymmetric hydrogenation approach for the total synthesis of biologically active (R,L) A. ludens host marking pheromone (HMP). The use of a novel Ir(i)-complex and a chiral P,N-ligand resulted in excellent enantioselectivities of up to 94% ee. The streamlined synthetic route involving seven reaction steps offers improved efficiency and shorter synthesis timelines compared to previous methods.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Multidisciplinary Sciences
Cheng Sheng, Zheng Ling, Yicong Luo, Wanbin Zhang
Summary: N,O-acetals are important building blocks for many synthetic intermediates, natural products, and pharmaceutical drugs. The authors developed a Cu-catalyzed asymmetric addition of alcohols to beta,gamma-alkynyl-alpha-imino esters, providing linear chiral N,O-ketals with high enantioselectivity.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ke Zhang, Xiao-Fei Liu, Wen-Zhen Zhang, Wei-Min Ren, Xiao-Bing Lu
Summary: The direct electrocarboxylation of N-acylimines with atmospheric CO2 has been achieved, providing substituted alpha-amino acids in high yields. The reaction is conducted efficiently using triethanolamine as an external reductant, and can be easily scaled up.
Article
Chemistry, Inorganic & Nuclear
Jie Wei, Li-Wen Ning, Ya Li
Summary: A diastereoselective Mannich-type reaction of 2-alkoxy-2-fluoroacetate and N-(tert-butylsulfinyl)imines is reported, providing a straightforward route to α-alkoxy- α-fluoro- β-amino acids in good yields and moderate to high diastereoselectivities. This approach uses readily accessible starting materials and is operationally simple. The stereochemistry of the current reaction differs from that of the known addition of comparable nonfluorinated 2-alkoxycarboxylic esters to N-sulfinyl imines, suggesting an open transition state explanation.
JOURNAL OF FLUORINE CHEMISTRY
(2023)
Article
Chemistry, Physical
Charlie Verrier, Nurtalya Alandini, Cristofer Pezzetta, Mauro Moliterno, Luca Buzzetti, Hamish B. Hepburn, Alberto Vega-Penaloza, Mattia Silvi, Paolo Melchiorre
Article
Chemistry, Multidisciplinary
Charlie Verrier, Sebastien Carret, Jean-Francois Poisson
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2018)
Article
Chemistry, Multidisciplinary
S. Jiang, C. Verrier, M. Ahmar, J. Lai, C. Ma, E. Muller, Y. Queneau, M. Pera-Titus, F. Jerome, K. De Oliveira Vigier
Article
Chemistry, Applied
Pascale Cividino, Charlie Verrier, Christian Philouze, Sebastien Carret, Jean-Francois Poisson
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Review
Biochemical Research Methods
Issa Diallo, Michel Seve, Valerie Cunin, Frederic Minassian, Jean-Francois Poisson, Sylvie Michelland, Sandrine Bourgoin-Voillard
EXPERT REVIEW OF PROTEOMICS
(2019)
Review
Chemistry, Organic
Chukuka Achuenu, Sebastien Carret, Jean-Francois Poisson, Florian Berthiol
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Benjamin Darses, Pascale Maldivi, Christian Philouze, Philippe Dauban, Jean-Francois Poisson
Summary: Bicyclic compounds with a quaternary stereogenic center were synthesized using asymmetric intramolecular Buchner reaction with high yields and enantioselectivity. X-ray crystallography revealed unexpected behavior in the crystal structure, including equilibrating valence isomers in the solid state, and DFT calculations supported these findings.
Article
Chemistry, Organic
Audrey Viceriat, Isabelle Marchand, Sebastien Carret, Jean-Francois Poisson
Summary: The synthesis of gamma-lactams using ketenes and aziridines or imines as precursors is practical, scalable, and yields high results. This method provides high regio- and diastereoselectivity on a wide range of substrates and high stereoselectivity when using enantiopure aziridines.
Review
Chemistry, Organic
Chukuka Achuenu, Sebastien Carret, Jean-Francois Poisson, Florian Berthiol
Summary: Chiral alpha-tertiary amines, a motif found in various natural products, drugs, and drug candidates, can be synthesized by adding organometallic reagents or other nucleophiles to chiral N-sulfinylketimines. This synthetic strategy has wide applications in the synthesis of biologically active compounds.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Michael Andresini, Sebastien Carret, Leonardo Degennaro, Fulvio Ciriaco, Jean-Francois Poisson, Renzo Luisi
Summary: This study reports a multistep continuous flow synthesis method for the preparation of poorly explored NH2-sulfinamidines by nucleophilic attack of organometallic reagents. The method allows for the synthesis of the target compounds under mild conditions via a highly chemoselective halogen-lithium exchange reaction, and the synthetic potential of the methodology was evaluated.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Rayhane Hammami, Pascale Maldivi, Christian Philouze, Sebastien Carret, Benjamin Darses, Soufiane Touil, Jean-Francois Poisson
Summary: A variety of 4-phosphinylpyrrolidin-3-ones were synthesized via a [3+2] cycloaddition reaction between aryl aldonitrones and phosphinylallenes. The products were obtained as unique 4,5-trans diastereomers in yields ranging from 47% to 80% for 23 examples. Chiral racemic allenes exhibited a moderate 2:1 to 4:1 2,5-diastereoselectivity. Under the reaction conditions, the cycloadducts undergo a rearrangement to selectively afford the corresponding pyrrolidin-3-ones. DFT calculations provided insights into the mechanism involving the homolytic cleavage of the N-O bond of the cycloadduct.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Lianjie Wang, Charlie Verrier, Mohammed Ahmar, Yves Queneau
