Article
Chemistry, Organic
Takumi K. Suzuki, Masahiro Yamanaka, Takayoshi Arai
Summary: This study reports the asymmetric iodoetherification reaction of unfunctionalized alkenes and its catalyst triZn-II. The reaction shows high enantioselectivity and provides a new platform for the synthesis of chiral morpholines.
Review
Chemistry, Organic
Wang Haiqing, Yang Shuang, Zhang Yuchen, Shi Feng
Summary: The article discusses the application and related issues of o-QMs and summarizes the rapid development of catalytic asymmetric reactions using o-hydroxybenzyl alcohols as precursors. It also highlights the potential of these reactions in synthesizing chiral oxygen-containing heterocycles and arylmethane derivatives.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Iain R. Miller, Neville J. McLean, Gamal A. Moustafa, Vachiraporn Ajavakom, Stephen C. Kemp, Richard K. Bellingham, Nicholas P. Camp, Richard C. D. Brown
Summary: An asymmetric synthetic route to (-)-galanthamine, a pharmacologically active alkaloid used for treating early onset Alzheimer's disease, was successfully established with high levels of stereocontrol using transition-metal-mediated reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Renren Li, Haocheng Zhang, Bangkui Yu, Hanmin Huang
Summary: A novel palladium-catalyzed cascade annulative aminomethylamination of diene-tethered enynes with aminals is reported. This method allows for the efficient synthesis of functionalized benzofulvenes with excellent chemo- and regioselectivities, as well as high atom economy. Mechanistic studies reveal the preferential reaction of alkylpalladium species with 1,3-enyne over 1,3-diene in initiating the cyclizative aminomethylamination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Lenin Kumar Verdhi, Asit Ghosh, Natalia Fridman, Alex M. Szpilman
Summary: A copper and chiral nitroxide co-catalyzed aerobic enantioselectiveoxidation process has been developed for the synthesis of axially chiral molecules. Two complementary atroposelective approaches, oxidative kinetic resolution (OKR) and desymmetrization, were studied using ambient air as the terminal oxidant. OKR results in optically pure compounds with er up to 3.5:96.5 and 5.5:94.5 for rac-N-arylpyrrole alcohols and rac-biaryl alcohols, respectively. Desymmetrization of prochiral diols produces axially chiral biaryl compounds with er up to 99:1.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Weilin Wang, Youliang Wang
Summary: In this study, a novel reaction method using diaryliodonium salts to promote multicomponent trifunctionalization of alkynes was reported. The reaction showed high selectivity in functionalizing alkynes and generated a diverse range of complex structures.
Letter
Chemistry, Organic
Zhengyu Han, Han Zhuang, Luning Tang, Yu Zang, Wengang Guo, Hai Huang, Jianwei Sun
Summary: A catalytic asymmetric allylic substitution/isomerization process with central chirality transposition has been developed. This process utilizes the ambident reactivity of the 2-indole imine methide generated in situ from racemic tertiary indolylmethanols, allowing regioselective formation of a C-C bond at the 3 position and enantiocontrolled construction of a stereogenic center at the 2-benzylic position.
Article
Chemistry, Multidisciplinary
Zhang-Long Yu, Yong-Feng Cheng, Ji-Ren Liu, Wu Yang, Dan-Tong Xu, Yu Tian, Jun-Qian Bian, Zhong-Liang Li, Li-Wen Fan, Cheng Luan, Ang Gao, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: Transition-metal-catalyzed enantioselective functionalization of acyl radicals has been achieved through Cu(I)-catalyzed enantioselective desymmetrizing C-O bond coupling. This reaction shows broad substrate scope, allowing for the synthesis of enantioenriched esters with challenging acyclic tetrasubstituted carbon stereocenters. With subsequent transformations, this reaction provides a convenient strategy for the rapid preparation of chiral C3 building blocks, especially from glycerol, which is industrially relevant. Mechanistic studies support the proposed C-O bond coupling of acyl radicals.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Taichiro Touge, Hideki Nara, Michio Kida, Kazuhiko Matsumura, Yoshihito Kayaki
Summary: Efficient dynamic kinetic resolution of cyclic halohydrins was achieved by asymmetric transfer hydrogenation of racemic alpha-haloketones using bifunctional oxo-tethered Ru(II) catalysts. The catalyst could produce chiral alcohols with various functional groups with excellent diastereo- and enantioselectivities, providing a concise synthetic approach to a dopamine D3 receptor ligand, (+)-PHNO.
Article
Chemistry, Organic
Tinghui Zhang, Ziwei Zhong, Zi Zeng, Zitong Zhu, Fei Wang, Yuxin Zhang, Xiaohua Liu, Maoping Pu, Xiaoming Feng
Summary: The asymmetric synthesis of enantioenriched C3-arylated oxindoles has been achieved via the Friedel-Crafts alkylation of 3-bromo-3-substituted oxindoles with arenes and heteroarenes, using a chiral N,N'-dioxide/transition metal complex as the catalyst.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yuan-Yuan Gao, Chun-Lin Zhang, Lei Dai, You-Feng Han, Song Ye
Summary: The unprecedented dynamic kinetic resolution (DKR) of hemiaminals without alpha-hydrogen was developed via N-heterocyclic carbene catalyzed O-acylation, resulting in high yields of esters with good to high enantioselectivities.
Article
Chemistry, Organic
Jian Song, Wen-Hua Zheng
Summary: A highly enantioselective method for the kinetic resolution of racemic tertiary alcohols has been developed using chiral organotin-catalyzed intermolecular acylation. The process can be carried out under mild reaction conditions and has a broad substrate scope, allowing for the separation of the corresponding products and highly enantioselective recovery of tertiary alcohols with s factors up to >200.
Article
Chemistry, Organic
Zheye Zhang, Jiaining Liu, Shang Gao, Bo Su, Ming Chen
Summary: We describe the stereoselective syntheses of (E)- and (Z)-crotylboronates with alpha,alpha-disubstitution. The alkylation reaction exclusively occurs at the alpha position to the boryl groups in the starting crotylboronates, resulting in the desired boronates while maintaining the original alkene geometries. The resulting alpha,alpha-disubstituted crotylboronates can undergo aldehyde addition to afford allylated products with high stereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tobias Koengeter, Can Qin, Binh Khanh Mai, Qinghe Liu, Yucheng Mu, Peng Liu, Amir H. Hoveyda
Summary: This paper presents a stereoretentive strategy for catalytic cross-metathesis reaction between tri-, Z- or E-di, or monosubstituted olefins and Z- or E-2-bromo-2-butene, leading to the formation of various trisubstituted alkenyl bromides. The method is applicable for the generation of products containing polar moieties or sterically hindered alkenes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Shang Gao, Jiaming Liu, Ming Chen
Summary: The study successfully synthesized compounds with high optical purity through catalytic asymmetric reactions, including (Z)-delta-hydroxymethyl-anti-homoallylic alcohols and alpha,beta-unsaturated aldehydes. Enantioconvergent pathways were utilized to achieve excellent optical purity.