Article
Chemistry, Multidisciplinary
Bin Shi, Jia-Bin Liu, Ze-Tian Wang, Liang Wang, Yu Lan, Liang-Qiu Lu, Wen-Jing Xiao
Summary: This study presents a new method for the synthesis of chiral endocyclic allenes with high efficiency and enantioselectivity, using a relay strategy that combines Pd-catalyzed [3+2] annulation and enyne-Cope rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chi Yang, Tian-Rui Wu, Yan Li, Bing-Bing Wu, Ruo-Xing Jin, Duo-Duo Hu, Yuan-Bo Li, Kang-Jie Bian, Xi-Sheng Wang
Summary: A novel method for facile synthesis of axially chiral styrene-type carboxylic acids has been developed, demonstrating excellent yield, stereocontrol, and substrate scope. The produced axially chiral styrene-type carboxylic acids have shown potential as chiral ligands or catalysts in asymmetric synthesis, as successfully applied in Cp*Co-III-catalyzed asymmetric C-H activation reactions.
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
Maximilian Kaiser, Michael Steinacher, Florian Lukas, Peter Gaertner
Summary: A general protocol for the europium-catalyzed rearrangement of aryl-pentadienyl-ethers is described, where the mode of rearrangement and product formation is determined by the substituent para to the phenol. The reaction undergoes a [3,3] rearrangement to form a prochiral branched diene when the para-position is occupied, and a [5,5] rearrangement to form a linear conjugated diene when the para-position is free.
Article
Chemistry, Organic
Chengqiang Cao, Yi Yang, Xin Li, Yunxia Liu, Hui Liu, Zengdian Zhao, Lei Chen
Summary: The reaction, catalyzed by palladium, efficiently constructs two new bonds with high yields, while the alkene group is easily functionalized, leading to the formation of products with a unique structure that is difficult to synthesize.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Songjin Guo, Jiayi Chen, Mingjun Yi, Liuli Dong, Aijun Lin, Hequan Yao
Summary: A highly efficient synthesis of unsymmetrical 3,3'-diindolylmethanes has been developed by palladium-catalyzed cascade Heck/cyclization reaction, allowing for the formation of one C-N bond, two C-C bonds and two new rings in one-pot. Precursors allenamides and o-ethynylanilines were utilized to generate in situ indole skeletons, and modification of the methylene unit of diindolylmethane was achieved by treatment with oxidant and silyl nucleophiles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shengbiao Yang, Chunyang Liu, Xiaoyan Shangguan, Yan Li, Qian Zhang
Summary: An unprecedented copper-catalyzed four-component reaction has been developed for the efficient synthesis of a wide range of imide derivatives.
Article
Chemistry, Multidisciplinary
Dong Wei, Han-Yu Lu, Han-Zhe Miao, Chen-Guo Feng, Guo-Qiang Lin, Yingbin Liu
Summary: An efficient and environmentally friendly method for preparing substituted indene derivatives using water as the sole solvent has been developed. This reaction can be conducted under air, tolerates a wide range of functional groups, and can be easily scaled up. Bioactive natural products like indriline can be synthesized using this protocol. Preliminary results show the possibility of achieving enantioselectivity.
Article
Chemistry, Organic
Aleksi Eronen, Martin Nieger, Tommi A. Kajander, Timo Repo
Summary: A modular synthetic method is reported for the preparation of diaryl-substituted cyclohexenone acids starting from phenyl pyruvate and suitable enones. When the reaction is carried out in alkaline tert-butanol or toluene solutions in microwave-assisted conditions, mainly anti configuration products are obtained with up to 86% isolated yield. However, when the reaction is carried out in alkaline water, a mixture of products with anti and syn conformations is obtained with up to 98% overall isolated yield. The product with anti conformation forms by a hemiketal-oxy-Cope type [3,3]-sigmatropic rearrangement-intramolecular aldol condensation route, while the syn product forms by an intermolecular aldol condensation-electrocyclization (disrotatory type) route.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Weiping Zhou, Arnaud Voituriez
Summary: The asymmetric total synthesis of two sesquiterpenoids, (-)-HM-3 and (-)-HM-4, isolated from a phytopathogenic fungus, has been achieved using a gold-catalyzed [3,3]-sigmatropic rearrangement of sulfonium as a key step. A high enantiomeric excess of 96% was observed in the chirality transfer from the chiral sulfoxide substrate to the newly formed quaternary stereogenic center. The implementation of this efficient methodology enabled the isolation of the two natural products in just 7-8 chemical steps with overall yields of 12-16%.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Aleksei N. Golikov, Chibeom Seo, Jae Hwan Lee, Sangho Koo
Summary: Palladium-catalyzed S-allylation reaction can be used to synthesize versatile dienyl benzothiazolyl sulfides, suitable for xanthophyll synthesis. The reaction shows high selectivity towards free allylic alcohols and can be used to synthesize compounds suitable for xanthophyll synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Chao Liu, Jiahao Wu, Xiangwen Tan, Jinhui Zhang, Wanqing Wu, Huanfeng Jiang
Summary: In this study, the intermolecular oxyamination reaction of aromatic amines and unactivated alkenyl carbonyl compounds under palladium catalysis was successfully achieved. Both primary and secondary aromatic amines efficiently yielded the corresponding β-arylamino-γ-lactones. The key step in this process involved a Pd-II/Pd-IV catalytic cycle incorporating a 1,2-(C-N)/(C-O) dyotropic rearrangement. The reaction exhibited mild reaction conditions and good functional group compatibility.
Article
Chemistry, Physical
Tristan Delcaillau, Hendrik L. Schmitt, Philip Boehm, Eric Falk, Bill Morandi
Summary: The intramolecular carbothiolation of unsaturated hydrocarbons using a palladium-NHC catalyst was reported. The reaction showed excellent tolerance and chemoselectivity, and could be applied to the synthesis of various sulfur-containing compounds.
Article
Chemistry, Organic
Raphael K. Klake, Joshua D. Sieber
Summary: In this study, a Cu-catalyzed aminoallylation of aldehyde electrophiles through reductive coupling was developed by avoiding the competitive reduction of the aldehyde electrophile by a CuH catalyst. This process resulted in a highly diastereo- and enantioselective synthesis of chiral 1,2-aminoalcohols with secondary alcohol substitution. Cleavage of the N substituents on the reaction products allowed access to the other diastereomer of the aminoalcohol, which was studied in the context of a synthesis of eligulstat.
Article
Chemistry, Organic
Lei Wang, Shuaijie Wu, Shuting Zhang, Qianqian Hu, Qiang Wang, Jing Sun, Ying Han, Chao-Guo Yan
Summary: A highly efficient palladium-catalyzed allenamide allylic alkylation of sulfenate anions under mild conditions is demonstrated, providing a practical protocol to access various sulfoxide-containing heterocyclic compounds. The transformation features a broad substrate scope, good functional group tolerance, easy scalability, and convenient synthetic transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
