Article
Chemistry, Organic
Tian-Yuan Zhao, Ke Li, Liang-Liang Yang, Shou-Fei Zhu, Qi-Lin Zhou
Summary: The highly enantioselective and diastereoselective nickel-catalyzed desymmetrizing cyclization of 1,6-dienes using chiral spiro phosphoramidite ligands provides a new atom- and step-economic approach to chiral spiro lactones and analogues bearing a quaternary stereo-center, which holds significant synthetic application value.
Article
Chemistry, Organic
Ming Huang, Changsheng Zhou, Ke-Fang Yang, Ze Li, Guo-Qiao Lai, Pinglu Zhang
Summary: This study developed an effective catalyst for the hydroborylation of cyclopropenes, resulting in the formation of cyclopylboronates that can be transformed into versatile cyclopropanes. This method works under mild reaction conditions in an open-air atmosphere and can be easily scaled up. Control experiments provide key insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhehui Liao, Jiantao Zhang, Tongxiang Cao, Shifa Zhu
Summary: A series of highly strained bicyclo[3.n.1]alkenones have been successfully synthesized with good-to-excellent enantioselectivities and moderate-to-good yields via copper-catalyzed formal [3+3] cycloaddition. The versatile chiral cycloadducts could be selectively converted into various valuable bridge systems, showing great potential for the construction of natural and bioactive compounds containing a [3.n.1] moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Maddalen Agirre, Tamara Bello, Jinxiu Zhou, Maria de Gracia Retamosa, Fernando P. Cossio
Summary: This study presents a method for the asymmetric synthesis of bicyclic highly substituted tetrahydropyrans, catalyzed by unnatural gamma-dipeptides based on densely substituted L-and D-proline derivatives. The one-pot reaction involves a ketone, a nitroalkene, and an aldehyde, resulting in an octahydro-2H-chromene scaffold. Monomeric species synthesized from which the y-dipeptides cannot catalyze the reaction, indicating the emergent nature of the catalytic behavior of these dimeric species.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Maddalen Agirre, Tamara Bello, Jinxiu Zhou, Maria de Gracia Retamosa, Fernando P. Cossio
Summary: The asymmetric synthesis of highly substituted tetrahydropyrans was achieved using unnatural gamma-dipeptides based on densely substituted L- and D- proline derivatives as catalysts. The dimeric species derived from these gamma-dipeptides showed emergent catalytic behavior in the one-pot reaction involving a ketone, a nitroalkene, and an aldehyde.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Martin Kocurik, Jan Bartacek, Pavel Drabina, Jirci Vana, Jan Svoboda, Lenka Husakova, Vladimir Finger, Michaela Hympanova, Milos Sedlak
Summary: This study presents an improved synthetic route for a ligand that can be used as a highly active and enantioselective catalyst. The immobilized catalyst exhibited stability and high turnover numbers, providing valuable insights into the development of continuous flow reactors for the synthesis of benzosultams.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, Organic
Wei Wu, Shunli Wen, Xinyu Zhang, Qi Lin, Zhiqiang Weng
Summary: A highly efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives is reported via a silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate. Various types of alpha-(heteo)aryl, alkyl, alpha-aryl, and alpha,beta-disubstituted vinyl azides can participate in this transformation. The proposed reaction mechanism involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N-C-1 cleavage, and elimination.
Article
Chemistry, Organic
Xinghua Wang, Shi-Jun Li, Ya-Nan Wang, Donghui Wei, Yu Lan
Summary: Desymmetrizing reactions of olefins catalyzed by N-Heterocyclic carbene (NHC) have been rapidly developing, but the origins of the chemo- and stereoselectivities in these reactions are still poorly understood. This study proposes a mechanistic map to predict how these selectivities are controlled by different active intermediates and contradicts a previous proposition regarding the determination of product structures by a transformation between a pair of isomers.
Article
Chemistry, Multidisciplinary
Krishna Kumar Gollapelli, Vaibhav B. Patil, Allam Vinaykumar, Rambabu Chegondi
Summary: A highly stereoselective desymmetrization reaction of 2-alkynylbenzaldehyde-tethered cyclohexadienones catalyzed by Rh(i) has been developed for the convergent construction of complex epoxy-bridged polycyclic ring systems. The process involves intramolecular Huisgen-type [3+2] cycloaddition, leading to the formation of five contiguous stereocenters with excellent exo-selectivity. Asymmetric induction is achieved for the first time in Rh(i)-catalyzed 1,3-dipolar cycloaddition using a readily accessible chiral diene as the ligand.
Article
Chemistry, Organic
Kotaro Ikeda, Shingo Harada, Yoshinori Hashimoto, Haruka Homma, Masato Kono, Nadine Zumbraegel, Harald Groeger, Tetsuhiro Nemoto
Summary: In this study, an optically active isoquinuclidine with four chiral carbon centers was obtained using enzymatic desymmetrization. Additionally, a pentacyclic intermediate for catharanthine was synthesized in an enantioenriched form through late-stage construction of the common Iboga scaffold.
Article
Chemistry, Organic
Qi Xu, Huan Zhang, Fang-Bei Ge, Xiao-Mei Wang, Peng Zhang, Chuan-Jun Lu, Ren-Rong Liu
Summary: In this study, we demonstrate that copper(I) catalysis using a bis(phosphine) dioxide ligand can efficiently catalyze the desymmetric C-H arylation of prochiral bipyrroles with excellent enantioselectivities. More than 50 nitrogen-nitrogen atropisomers were achieved in good to excellent yields. The mild reaction conditions and good functional group compatibility on arenes and diaryliodonium salts make this method highly versatile.
Article
Multidisciplinary Sciences
Jia-Lei Yan, Rakesh Maiti, Shi-Chao Ren, Weiyi Tian, Tingting Li, Jun Xu, Bivas Mondal, Zhichao Jin, Yonggui Robin Chi
Summary: In this study, a chiral solution utilizing N-heterocyclic carbene (NHC) catalyst was developed for the preparation of axially chiral styrenes with high enantioselectivity and excellent yields. The sulfone and carboxylic ester moieties in the styrenes are common functional groups in bioactive molecules and asymmetric catalysis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Qijian Ni, Zhiming Zhu, Yanjun Fan, Xiaoyun Chen, Xiaoxiao Song
Summary: The research has successfully developed an organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition method for adding indolizines to cyclopentenediones to obtain the desired products. The utility of the method was demonstrated through various late-stage functionalizations.
Article
Chemistry, Organic
Stefan Malatinec, Eva Bednarova, Hiroki Tanaka, Martin Kotora
Summary: This study presents a catalytic and highly enantioselective ring-opening reaction of epoxides, utilizing newly designed chiral bipyridine ligands. A Sc-complex with a newly developed bipyridine ligand demonstrated high reactivity and stereocontrol in the desymmetrization of meso-epoxides with various alcohols, achieving enantioenriched 1,2-alkoxyalcohols with high e.r. values. Additionally, attempted ring-opening of meso-epoxides with anilines showed lower enantioselectivity, dependent on the electronic effect of substituents on the aromatic ring.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuri Tulchinsky, Sebastian Kozuch, Prasenjit Saha, Assaf Mauda, Gennady Nisnevich, Mark Botoshansky, Linda J. W. Shimon, Mark Gandelman
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Organic
Prasenjit Saha, Arnab Biswas, Nagaraju Molleti, Vinod K. Singh
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Multidisciplinary
Tapas Das, Anirban Kayet, Ruchika Mishra, Vinod K. Singh
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Organic
Jun Park, Dong-Hyun Kim, Tapas Das, Cheon-Gyu Cho
Article
Chemistry, Multidisciplinary
Yuri Tulchinsky, Sebastian Kozuch, Prasenjit Saha, Mark Botoshansky, Linda J. W. Shimon, Mark Gandelman
Review
Chemistry, Multidisciplinary
Susanta Kumar Manna, Tapas Das, Shubhankar Samanta
Review
Chemistry, Organic
Madan Sau, Kshitiz Verma, Tapas Das
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2020)
Review
Chemistry, Multidisciplinary
Tapas Das, Madan Sau, Bishnu Daripa, Dipanjan Karmakar, Sayan Chakraborty
Review
Chemistry, Multidisciplinary
Tapas Das
Review
Chemistry, Multidisciplinary
Arunima Das, Seema Thakur, Tapas Das
Summary: Indole-2-carboxaldehydes play a crucial role in the synthesis of diverse indole scaffolds, providing a foundation for the synthesis of biologically active compounds.
Review
Chemistry, Multidisciplinary
Saradindu Debnath, Syaleena Parveen, Priyankar Pradhan, Ipsita Das, Tapas Das
Summary: Nitrogen heterocycles are vital compounds found in nature or synthesized, playing essential roles in living systems and having potential applications in drugs and materials.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Seema Thakur, Arunima Das, Tapas Das
Summary: Cycloadditions are considered important chemical reactions, with nitrones reacting with various substrates to generate diverse heterocyclic rings that have wide-ranging applications.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Sk Asraf Ali, Suresh Kumar Mondal, Tapas Das, Susanta Kumar Manna, Anirban Bera, Debabrata Dafadar, Sourenjit Naskar, Mijanur Rahaman Molla, Shubhankar Samanta
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
