Article
Chemistry, Organic
Nicolas S. S. George, Marharyta Kosiuha, Alexandre Moquette, Christophe Parsy
Summary: We describe a versatile methodology for the synthesis of 1,2-sulfoximidoyl ethanols through a regioselective epoxide ring-opening reaction. The chemoselectivity of the reaction is assessed by competition reactions with other nucleophiles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Velautham Saravanan, Masilamani Jeganmohan
Summary: This study describes a palladium-catalyzed tandem reaction of 7-oxabenzonorbornadienes with organic carboxylic acids, which produces cis-1,2-dihydro-l-naphthyl derivatives with moderate to good yields and high diastereoselectivity. A proposed reaction mechanism involving syn acylation, insertion, and diastereoselective ring-opening with 7-oxabenzonorbornadienes explains the reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Lantao Liu, Fangyuan Cheng, Chenxiang Meng, An-An Zhang, Mingliang Zhang, Kai Xu, Naoki Ishida, Masahiro Murakami
Summary: A Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates. This method provides a convenient approach to chiral 2,3-dihydrobenzofurans with excellent enantioselectivities, and has been applied in the concise synthesis of analogues of cannabinoid receptor 2 agonists.
Article
Chemistry, Multidisciplinary
Junjie Meng, Hui He, Qianru Liu, Hanhong Xu, Huicai Huang, Shao-Fei Ni, Zhaodong Li
Summary: A PdII-catalyzed domino enantioselective desymmetrizative coupling of 7-azabenzonorbornadienes with alkynylanilines is described, which generates valuable functionalized compounds with excellent enantio- and diastereo-selectivity. The method allows the construction of multiple covalent bonds and stereocenters in an efficient and atom-economical manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Xi-Chao Wang, Bo Li, Cheng-Wei Ju, Dongbing Zhao
Summary: Transition metal-catalyzed reactions of silacyclobutanes with a variety of pi units have become a straightforward and efficient approach to access structurally diverse organosilicon compounds. However, the reaction of silacyclobutanes with alkynes still faces limitations, such as challenging internal alkynes, expensive catalysts, and lack of control over chemodivergence. In this study, a nickel-catalytic system is introduced, which overcomes these limitations and provides complementary substrate scope, ligand-controlled chemodivergence, and low cost. Ligand steric effects play a crucial role in determining the selectivities of different reaction pathways.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Dong Gao, Lei Jiao
Summary: This study presents an efficient method for constructing indoline structures with a C2-quaternary stereocenter and controlling the migrating group through aza-semipinacol rearrangement. It enables the divergent access to dearomatized indole derivatives with either a C3- or a C2-quaternary stereocenter.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jeanne Masson-Makdissi, Liher Prieto, Xavier Abel-Snape, Mark Lautens
Summary: This study demonstrates the feasibility and advantages of combining two distinct asymmetric transition-metal-catalyzed reactions in one pot, effectively converting simple allyl enol carbonate precursors into enantioenriched cyclic ketones. Despite the challenges in controlling stereoselectivity, the products are obtained with high enantiomeric excesses exceeding 99% ee, surpassing those obtained from individual reactions. Additionally, the one-pot reaction is enantio- and diastereodivergent, allowing easy access to all stereoisomers from the same starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jiaan Shao, Ke Shu, Shuangrong Liu, Huajian Zhu, Jiankang Zhang, Chong Zhang, Ling-Hui Zeng, Wenteng Chen
Summary: A palladium-catalyzed ring-opening reaction of 2H-azirines with hydrazones has been developed, providing an alternative route for the construction of various polysubstituted pyrazoles with a wide substrate scope. A plausible mechanism is proposed for this reaction, enriching the chemical conversion of 2H-azirines.
Article
Chemistry, Multidisciplinary
Taku Kitanosono, Tomoya Hisada, Yasuhiro Yamashita, Shu Kobayashi
Summary: Metal-bound water molecules have been recognized as a new aspect of soft Lewis acid catalysis. A chiral palladium aqua complex was constructed using a chiral ligand and hydrogen-bond donor, allowing efficient functionalization of carbon-hydrogen bonds of indoles in water. The use of aqueous environments enabled highly enantioselective reactions of sigma-indolylpalladium intermediates, presenting a potentially powerful approach for organometallic transformations under mild conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jun-An Xiao, Huan Zhang, Xue-Ling Luo, Ru-Fang Meng, Wei Wang, Wei-dong Lu, Wei Su, Chenxiang Lin, Peng-Ju Xia, Hua Yang
Summary: A palladium-catalyzed ring-opening [3 + 2]-annulation reaction was developed for the synthesis of seven-membered benzosultams from spirovinylcyclopropanyloxindoles and cyclic N-sulfonylimines. The reaction yielded a wide range of compounds with both a quaternary center and axially chiral biaryl scaffolds, with an average yield of 87% and moderate to excellent diastereoselectivities. Enantioenriched benzosultams were also successfully synthesized in good yields with excellent atropoenantioselectivities using the Pd-2(dba)(3)/(S,S,S)-SKP ligand. The practical utility of this method was demonstrated through gram-scale reactions and diversified synthetic transformations.
Article
Chemistry, Physical
Changhui Lu, Yueping Lin, Minyan Wang, Jiaming Zhou, Shuo Wang, Huanfeng Jiang, Kai Kang, Liangbin Huang
Summary: In this study, a nickel-catalyzed ring-opening transformation of benzofuran with silanes was reported, selectively giving ortho-alkene-, branched/linear alkyl silane-, and alkenyl silane-substituted phenol derivatives. This reaction provides a highly desirable and underdeveloped method for the construction of valuable phenol derivatives.
Article
Chemistry, Multidisciplinary
Hai Huang, Tianyu Zhang, Jianwei Sun
Summary: The use of soft carbon nucleophiles to open oxetanes has been developed for efficient C-C bond formation. Silyl ketene acetals and styrene-based carbon nucleophiles can generate a wide range of highly oxygenated molecules in the presence of catalysts, which are key substructures in natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Katarina Stefkova, Michael G. Guerzoni, Yara van Ingen, Emma Richards, Rebecca L. Melen
Summary: Here, a mild, transition-metal-free, highly diastereoselective Lewis acid catalyzed methodology for the synthesis of isoxazolidine-based diazo compounds from the reaction between vinyldiazo esters and nitrones is reported. Interestingly, the diastereoselectivity of the isoxazolidine products is found to be contrasting to previous metal-catalyzed reactions. Furthermore, the same catalyst can be used with enol diazo esters, leading to the formation of Mukaiyama-Mannich products. These diazo products can be further functionalized to generate benzo[b]azepine and pyrrolidinone derivatives.
