Article
Chemistry, Multidisciplinary
Giuseppe Zuccarello, Suzanne M. Batiste, Hyungdo Cho, Gregory C. Fu
Summary: Due to increasing interest in the pharmaceutical industry, the synthesis of chiral alpha-aminoboronic derivatives has become an important challenge. In this study, we demonstrate the enantioselective synthesis of these derivatives using a chiral copper catalyst generated from commercially available components. Mechanistic studies were also conducted to optimize the process and provide insights into the reaction mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Pilar Elias-Rodriguez, Ana T. Carmona, Antonio J. Moreno-Vargas, Inmaculada Robina
Summary: In this study, iminosugar derivatives containing a pyrrolidine-phosphine moiety were synthesized and used as catalysts in the [3 + 2] cycloaddition reaction between alkyl allenoates and electron-deficient imines. The results demonstrated that under appropriate conditions, 1,2,3,5-tetrasubstituted pyrrolines with high yields and good diastereoselectivities were obtained.
Article
Chemistry, Organic
Vincenzo Battaglia, Sara Meninno, Alessandra Lattanzi
Summary: In this study, a novel and concise method for the synthesis of the commonly used antiplatelet drug Plavix was developed. Through careful optimization of reaction conditions, a high synthesis yield and selectivity were achieved.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Elisa Brambilla, Camilla Pozza, Silvia Rizzato, Giorgio Abbiati, Valentina Pirovano
Summary: This paper describes an enantioselective phosphine-catalyzed [3+2] cycloaddition reaction between aza-aurones and allenoates. The reaction proceeds under mild conditions and offers 2-spirocyclopentyl indolin-3-one derivatives as a single gamma-isomer with high stereocontrol.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Anup Biswas, Avisek Ghosh, Rajat Shankhdhar, Indranil Chatterjee
Summary: Chiral analogues of squaramides have proved to be efficient asymmetric catalysts in the synthesis of acyclic and cyclic chiral molecules. By utilizing several bifunctional squaramides as catalysts, a wide range of cyclic molecules bearing multiple functionalities and stereocenters have been successfully synthesized.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Min Liu, Leijie Zhou, Wangyu Shi, Yimin Hu, Jianning Liao, Zeqing Duan, Wei Wang, Yongjun Wu, Bing Zheng, Hongchao Guo
Summary: The delta-sulfonamido-substituted enones were utilized as phosphine acceptors in the phosphine-catalyzed (4 + 2) annulation of 1,1-dicyanoalkenes. They acted as a four-membered synthon to react with 1,1-dicyanoalkenes under mild reaction conditions, producing piperidine derivatives in moderate to excellent yields with good to excellent diastereoselectivities.
Article
Chemistry, Multidisciplinary
Binghui Wang, Yilin Liu, Chenyang Jiang, Zheng Cao, Shanshan Cao, Xiaowei Zhao, Xu Ban, Yanli Yin, Zhiyong Jiang
Summary: Describes a chiral Bronsted acid-catalysed asymmetric hydrophosphinylation of 2-vinylazaarenes by secondary phosphine oxides. P-chiral 2-azaaryl-ethylphosphine oxides are synthesized with high yields and ees, allowing for flexible modulation of substituents. The resulting P-chiral tertiary phosphines from the reduction are confirmed as effective C-1-symmetric chiral 1,5-hybrid P,N-ligands, making these adducts valuable in asymmetric metal catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yuqi Zhu, Ting Zhou, Hong Zhang, Jieyin He, Hongguang Li, Ming Lang, Jian Wang, Shiyong Peng
Summary: This study reports a Rh(II)-catalyzed reaction method for the synthesis of α-aryl-β-aminocyclopropane carboxylic acid derivatives with stereo-isomeric centers using donor-acceptor carbenes derived from a-aryldiazoesters and vinylsulfonamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bo-Bo Gou, Yue Tang, Yan-Hong Lin, Le Yu, Qing-Song Jian, Huai-Ri Sun, Jie Chen, Ling Zhou
Summary: A new type of chiral all-carbon tetrasubstituted VQMs was successfully prepared via nucleophilic addition of 2-alkynylnaphthols to o-quinone methides or imines, catalyzed by chiral phosphoric acids. The method showed high efficiency and excellent diastereoselectivities and enantioselectivities, leading to the synthesis of naphthyl-2H-chromenes with axially and centrally chiral elements and axially chiral quinone-naphthols. The obtained axially chiral naphthols could further be converted into valuable phosphine ligands and other functional molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Rosa Lopez, Claudio Palomo
Summary: N,N-Diacylaminals are flexible molecular scaffolds commonly used as amide surrogates in peptidomimetics. Recently, their singularity as an N-acyl imine equivalent and hydrogen-bond donor has led to new synthetic opportunities, particularly in the field of asymmetric catalysis. This concept article highlights the diverse synthetic potential of N,N-Diacylaminals and provides the necessary elements for further developments.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Aleksandra Buchcic-Szychowska, Stanislaw Lesniak, Michal Rachwalski
Summary: A series of chiral aziridines with a phosphine moiety were synthesized and used as organocatalysts in the asymmetric intramolecular Rauhut-Currier reactions of p-quinone derivatives. The desired chiral phenols were obtained with high yields and satisfactory enantiomeric excess values.
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Casper L. Barlose, Niklas L. ostergaard, Rene S. Bitsch, Marc V. Iversen, Karl Anker Jorgensen
Summary: An enantioselective methodology for constructing trans-Diels-Alder scaffolds with up to five contiguous stereocenters is presented, utilizing a halogen effect and a novel discovered pseudo-halogen effect. The reaction involves an endo-selective, secondary-amine catalyzed Diels-Alder reaction followed by a subsequent S(N)2-like reaction at a tertiary center to obtain the trans-Diels-Alder scaffold. The mechanism was supported by experimental results and computational studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
