Article
Chemistry, Organic
Yiming Zhou, Ning Li, Wei Cai, You Huang
Summary: A new sequential reaction has been developed for the synthesis of tetra-substituted 2,3-dihydrofurans with generally excellent yields and good diastereoselectivities. Chiral propargyl sulfonium salt can also be used for the synthesis of optically active 2,3-dihydrofurans with good enantioselectivities. The reaction sequence is designed based on the in situ generated 107r-conjugated structures from the dearomatization of indole fragments and subsequent intramolecular 1,6-addition.
Article
Chemistry, Multidisciplinary
Zeynep Dilsad Susam, Merve Bozdemir, Gulsum Gundogdu, Cihangir Tanyeli
Summary: An asymmetric organocatalytic domino type Michael-S(N)2 reaction was developed to synthesize enantiomerically enriched dihydrofuran derivatives, demonstrating high efficiency and enantioselectivity.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Yi-Min Fan, Li-Juan Yu, Michael G. Gardiner, Michelle L. Coote, Michael S. Sherburn
Summary: The diene-transmissive hetero-Diels-Alder sequences involving carbonyl dienophiles are reported for the first time. High enantioselectivities are achieved through the optimization of a Pd2+ catalyst system. The reaction generates fused polycyclic systems containing both heterocycles and carbocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zhi-Wei Ma, Chuan-Chuan Wang, Xiao-Pei Chen, Bin Sun, Jing-Chao Tao, Quan-Jian Lv
Summary: A highly stereoselective methodology has been developed for the construction of dihydrofurans. The Michael addition/cyclization between cyclohexane-1,3-dione and alpha-bromonitroalkenes was smoothly carried out in the presence of a bifunctional squaramide catalyst to afford the desired dihydrofurans with high yields (90-94%) and good to high enantioselectivities (80-94% ee).
LETTERS IN ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guangxing Pan, Shaoheng Qin, Dawen Xu, Fritz E. Kuehn, Hao Guo
Summary: The photoinduced pericyclic cascade reaction described in this study provides a novel approach to oxabicyclo[4.2.0]octenes, involving [2 + 2]-photocycloaddition, base-promoted elimination, retro-4p-electrocyclization, [1,5]-H shift, and 4p-electrocyclization processes. This reaction exhibits broad substrate scope, good functional group tolerance, and excellent diastereoselectivity.
Article
Chemistry, Multidisciplinary
Yan-Bo Li, Hu Tian, Shuai Zhang, Jun-Zhao Xiao, Liang Yin
Summary: In this study, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines was developed, leading to the synthesis of aminophosphinites and P-chiral aminophosphinites. The reaction mechanism was proposed and further transformation to P-chiral phosphines was achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhi-Zhou Pan, Jia-Heng Li, Hu Tian, Liang Yin
Summary: A copper(I)-catalyzed asymmetric allylation of ketones with 2-aza-1,4-dienes has been demonstrated, providing a series of functionalized homoallyl tertiary alcohols with high to excellent enantioselectivity. The deprotonation of N-allyl-1,1-diphenylmethanimines is the rate-determining step in the reaction, generating nucleophilic allyl copper(I) species. The utility of this method has been demonstrated by the asymmetric synthesis of (R)-boivinianin A and (R)-gossonorol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Regis Guillot, Cyrille Kouklovsky, Boris Maryasin, Aurelien de la Torre
Summary: A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported, leading to the synthesis of bridged bicyclic lactones with high yields and enantioselectivities using a copper(II)-BOX catalytic system. Mechanistic studies suggest a stepwise mechanism, and the synthetic potential of the bridged bicyclic lactones is demonstrated through the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Meng-Die Li, Zi-Han Wang, Hui Zhu, Xin-Ru Wang, Jia-Run Wang, Tao-Yan Lin
Summary: In this study, the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates was reported. The method demonstrated practicality and attractiveness due to the use of readily available starting materials, mild reaction conditions, excellent selectivity, and broad substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Brian S. Daniels, Xintong Hou, Stephanie A. Corio, Lindsey M. Weissman, Vy M. Dong, Jennifer S. Hirschi, Shaozhen Nie
Summary: A copper catalyst is reported for the addition of phosphines to cyclopropenes at ambient temperature. Various cyclopropylphosphines with different steric and electronic properties can now be synthesized in high yields and enantioselectivities. Through a combined experimental and theoretical study, the mechanism is proposed to involve insertion of a Cu-I-phosphido into a carbon-carbon double bond.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xiuping Yuan, Yiliang Zhang, Yanfei Li, Jianjun Yin, Simin Wang, Tao Xiong, Qian Zhang
Summary: In this paper, a copper-catalyzed radical oxyboration reaction was reported, which allows for highly selective synthesis of enantioenriched trans-1,2-dioxygenation products. By developing a late-stage stereomutation strategy and optimizing reaction conditions, high diastereoselectivity and enantioselectivity were achieved. This method shows significant potential in the synthesis and modification of complex molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Di Ke, Lei Zhang, Xiuwen Zhong, Jiaan Shao, Yongping Yu, Wenteng Chen
Summary: This study reports an efficient synthesis method for 3,4-hydroxypyridinone (3,4-HOPO) using electrophilic activation via covalent bonds between boronic acid and 3-hydroxyl/4-carbonyl. The reaction proceeds well in water with high efficiency and tolerates various amine donors. Additionally, the synthesis of 3,4-HOPO compounds on a large scale was successfully achieved.
Article
Chemistry, Applied
Maxime Denis, Samuel Blais, Sylvain Canesi
Summary: A stereoselective synthesis of isolycoricidine, a natural product belonging to the Amaryllidaceae alkaloids family, was achieved. The study also conducted a synthetic investigation on the main core of lycoricidine, resulting in the formation of analogues and a diastereomer of dihydrolycoricidine. The research utilized various strategies including oxidative phenol dearomatization, stereoselective Heck process, selective dihydroxylation, stereoselective reductions, and oxidative retro-Michael procedure as an amine-deprotecting group strategy. In addition, the study highlighted the usefulness of hypervalent iodines in total synthesis of natural products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)