Review
Chemistry, Multidisciplinary
Rose Mary Philip, G. S. Susan Treesa, Salim Saranya, Gopinathan Anilkumar
Summary: This review summarizes the application of enantiopure aryl-sulfinamides in asymmetric methods for N-heterocycle synthesis, providing a general pathway to diverse piperidines, pyrrolidines, aziridines, and their derivatives through sulfinylimines.
Review
Chemistry, Multidisciplinary
Alexey V. Dobrydnev, Maria V. Popova, Yulian M. Volovenko
Summary: The literature on cyclic sulfinamides, known as sultims, published from 1989 to 2022 is summarized and reviewed. The information is divided into two sections, focusing on synthetic methods and chemical properties of cyclic sulfinamides. Detailed survey of reaction conditions and critical analysis of reaction mechanisms are provided. The data presented will be valuable for specialists in synthetic organic and pharmaceutical chemistry.
Article
Chemistry, Multidisciplinary
Saori Tsuzuki, Taichi Kano
Summary: In this study, an efficient method for preparing chiral sulfimides from easily available enantioenriched sulfinamides was reported. The key step involves a stereospecific oxygen-selective alkylation of enantioenriched sulfinamides using isopropyl iodide, K2CO3, and DMPU. The resulting chiral sulfinimidate esters are transformed to chiral sulfimides through nucleophilic addition of Grignard reagents under simple conditions. This method allows access to enantioenriched diaryl or dialkyl sulfimides bearing two similar carbon substituents, which are difficult to synthesize using previous methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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
Fei-Fei Zou, Zhen Luo, Yu-Ting Yang, Xin Zhuang, Chuan-Ming Hong, Zheng-Qiang Liu, Wan-Fang Li, Qing-Hua Li, Tang-Lin Liu
Summary: A regio- and chemoselective sulfonylation method was developed for the synthesis of multi-substituted allenyl sulfones using sulfinamides as the sulfonyl sources. The use of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as the solvent enabled the transformation to proceed under mild conditions without the need for additional catalysts or oxidants.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Daheng Wen, Qingshu Zheng, Chaoyu Wang, Tao Tu
Summary: A rare-earth-catalyzed transsulfinamidation method has been developed for the synthesis of diverse secondary and tertiary sulfinamides using primary sulfinamides and a variety of alkyl, aryl, and heterocyclic amines. The protocol is suitable for readily available primary and secondary amines without any modifications, demonstrating excellent catalytic activity and selectivity with Eu(OTf)(3) under mild reaction conditions, thus extending the applicability of rare-earth catalysis.
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Saori Tsuzuki, Taichi Kano
Summary: A metal- and additive-free reaction for the transsulfinamidation of N-unsubstituted sulfinamides and N-pivaloyl-protected sulfinamides with various amines is reported. The reaction proceeds by simply heating and provides both N-monosubstituted and N,N-disubstituted sulfinamides in good yields. Preliminary experiments also show that alcohols can be used as nucleophiles instead of amines, giving sulfinate esters.
Article
Chemistry, Organic
Saori Tsuzuki, Taichi Kano
Summary: This article summarizes the recent studies on the asymmetric synthesis of chiral sulfoximines and sulfimides from enantioenriched sulfinamides. Optically pure sulfoximines and sulfimides with various carbon substituents on their sulfur atom could be efficiently obtained.
Article
Chemistry, Organic
Milos Jabczun, Vladimir Nosek, Jiri Misek
Summary: We present a simple one-pot reductive protocol for synthesizing sulfinamides from sulfonyl chlorides, allowing for the preparation of sulfinamides with a wide range of functional groups. Additionally, we have expanded an existing oxidative pathway to sulfinamides starting from thiols. These methods offer a general strategy for the synthesis of sulfinamides from commonly available sulfur-based feedstock, providing a high structural and functional group diversity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Mengting Kou, Ziqiang Wei, Zhen Li, Bin Xu
Summary: A copper-catalyzed sulfinyl cross-coupling reaction of sulfinamides with aldehyde-derived N-tosylhydrazones is reported. This approach provides an efficient and novel way to construct structurally diverse sulfoxides, with broad substrate scope and compatibility with various functional groups and pharmacophores. Moreover, the reaction can be scaled up to gram scale and carried out in a one-pot fashion directly from aldehydes.
Article
Chemistry, Organic
Glebs Jersovs, Matiss Bojars, Pavel A. Donets, Edgars Suna
Summary: A synthetic method for densely substituted enantiopure cyclic sulfinamides with multiple consecutive stereogenic centers has been developed using a completely diastereoselective reaction sequence. The obtained scaffold can be transformed into chiral S-VI derivatives, such as sulfoximines and sulfonimidamides.
Article
Chemistry, Multidisciplinary
Yasu Chen, Xinxin Wu, Shan Yang, Chen Zhu
Summary: We have developed a novel method for asymmetric radical cyclization of alkenes via stereospecific homolytic substitution of sulfinamides. This reaction allows for the synthesis of a variety of cyclic sulfinamides with excellent stereocontrol. The protocol has broad functional group tolerance, high product diversity, and easy accessibility to feedstocks, providing a new pathway for the synthesis of chiral cyclic sulfinamides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Yichen Wu, Peng Wang
Summary: Optically active organosilanes have been demonstrated to be versatile chiral reagents in synthetic chemistry. Monohydrosilanes, which bear a Si-H bond, are especially unique due to their facile transformations through stereospecific bond-formation reactions. In addition, they have also been used as chiral reagents for alcohol resolution, chiral auxiliaries, mechanistic probes, and potential optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chun-Tai Hung, Chun-Wei Lu, Shi-Han Huang, Yin-Feng Lu, Hsiang-Chi Chou, Cheng-Che Tsai
Summary: This research utilizes chiral sulfinamides as nucleophiles in intramolecular allylic substitution and sequential aerobic oxidation with aza-Michael addition reactions, achieving good yields of chiral isoindolines and high diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)