Article
Chemistry, Organic
Barry M. Trost, Chuanle Zhu, Chloe Christine Ence
Summary: This study reports a palladium-catalyzed [3 + 2] cycloaddition using in situ generated sulfone-TMM species to construct various chiral cyclopentyl sulfones in a highly regio-, diastereo-, and enantioselective manner. The robust chiral diamidophosphite ligand is crucial for the reactivity and selectivities of this transformation, allowing for the construction of three chiral centers in a single step.
Article
Chemistry, Applied
Xue-Qi Wang, Fang-Fang Feng, Jing Nie, Fa-Guang Zhang, Jun-An Ma
Summary: An asymmetric decarboxylative Mannich reaction of phosphonate sultam-ketimines with malonic acid half esters is achieved using saccharide-derived bifunctional amino thiourea catalysis. This reaction provides access to a wide range of alpha-amino-beta-carboxylic phosphonates with N,P-containing tetrasubstituted stereocenters, achieving high enantioselectivity (78-99% ee). Further synthetic derivatizations can introduce amide, alcohol, and azetidine scaffolds to the core structures.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Chuanle Zhu, Yingying Cai, Huanfeng Jiang
Summary: Chiral sulfones, especially those compounds with sulfone groups directly connected to the chiral centers, are privileged building blocks in natural products and bioactive compounds. Various strategies have been developed for their asymmetric synthesis, including nucleophilic substitution, hydrosulfonation, cross-coupling reactions, and others, which are important for the synthesis of bioactive compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jing Li, Zhonglin Wei, Jungang Cao, Dapeng Liang, Yingjie Lin, Haifeng Duan
Summary: A highly enantioselective aza-Friedel-Crafts reaction of 1H-indoles with isatin-derived N-Cbz-ketimines catalyzed by quinine-derived phase-transfer catalysts was developed. Chiral 3-aminobisindole compounds containing a tetrasubstituted stereocenter were constructed in high yields (82-91%) and moderate to excellent enantioselectivities (46-94% ee).
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhikun Liang, Qinglei Chong, Fanke Meng
Summary: This method involves the catalytic generation of cobalt enolates from easily accessible cyclopropanols, followed by diastereo- and enantioselective additions to aldimines. The process leads to the formation of a wide range of beta-amino-ketones in high yields, with excellent diastereomeric and enantiomeric ratios, without the need for any stoichiometric amount of additives or reagents.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Applied
Eri Ogino, Satoru Kuwano, Takayoshi Arai
Summary: In this study, chiral catalyst AMB2 was used to successfully catalyze the asymmetric epoxidation of acrylonitriles, resulting in highly enantioselective chiral epoxides.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Weizhi Gu, Jindong Li, Kuiliang Li, Qi Sun, Tong Li, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Mannich reaction of 2-fluoroindanone with ketimine was developed using a chiral copper complex catalyst, resulting in the formation of a chiral tetrahedral center containing fluorine. The reaction yielded a series of fi-fluoroamine derivatives in excellent yields (73-94%) with high diastereoselectivities (>99:1 dr) and enantioselectivities (89-99%). Density functional theory calculations supported the proposed transition state.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lei Wang, Wenxin Lu, Jiwu Zhang, Qinglei Chong, Fanke Meng
Summary: In this study, an unprecedented cobalt-catalyzed regio-, diastereo- and enantioselective hydrosilylation of 1,3-dienes is presented, enabling the simultaneous construction of a carbon- and a silicon-stereogenic center. The generated chiral silanes exhibit high efficiency and stereoselectivity, and can be further functionalized to obtain valuable chiral building blocks.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zheng-Fei Li, Chong-Lin Zhu, Yun Zhang, Yun Yao, Chong-Dao Lu
Summary: A new Mannich reaction was developed to prepare 3-amino-3-substituted oxindoles containing a specific chiral carbon. Excellent stereocontrol was achieved through deprotonation and C-C bond formation, allowing for the construction of contiguous quaternary and tetrasubstituted stereocenters with high stereo-selectivity.
Article
Chemistry, Physical
Ruijie Mi, Xuepeng Zhang, Jinlei Wang, Haohua Chen, Yu Lan, Fen Wang, Xingwei Li
Summary: This study reports the rhodium-catalyzed enantioselective three-component coupling of arene, diene, and dioxazolone via C-H activation to produce chiral allylic amines. The electrophilic amination of the pi-allyl species is both regio- and enantio-determining in this carboamination reaction.
Article
Chemistry, Applied
I-Ting Chen, Ren-You Guan, Jeng-Liang Han
Summary: In this study, a catalytic asymmetric vinylogous Mannich/annulation/acylation reaction was developed for the synthesis of chiral spiro-oxindole piperidine derivatives with polyaromatic scaffolds. The reaction provided the desired products in good yields and high enantioselectivity. DFT computational calculations were used to explain the mechanism and origin of the observed enantioselectivity and O-acetylated products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xin Yu, Lingfei Hu, Wolfgang Frey, Gang Lu, Rene Peters
Summary: Catalytic allylic substitution is an important method in asymmetric synthesis to generate C-C bonds with enantioselectivity. However, a common limitation is the formation of allylic substitution products with (E)-configured C=C double bonds. In this study, a planar chiral palladacycle catalyst was used to achieve a diastereospecific reaction outcome, maintaining the C=C double bond geometry of the allylic substrates in highly enantioenriched products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Juanjuan Wu, Hongli Wu, Xinyu Liu, Yuekun Zhang, Genping Huang, Chun Zhang
Summary: A nickel-catalyzed reductive cross-coupling reaction has been developed for the synthesis of chiral α-CF3 ketones with high enantioselectivity and good functional group tolerance. The study of late-stage transformation demonstrated its applicability in preparing bioactive compounds. Control experiments further indicated the importance of the α-trifluoromethyl group in this reaction.
Article
Chemistry, Multidisciplinary
Wendian Li, Tilong Yang, Nan Song, Ruihao Li, Jiao Long, Lin He, Xumu Zhang, Hui Lv
Summary: A highly efficient method for asymmetric sequential hydrogenation of alpha,beta-unsaturated ketones has been developed, which enables the synthesis of chiral alcohols with two contiguous stereocenters in high yields and excellent enantioselectivity. Control experiments and DFT calculations revealed the reaction mechanism and factors affecting the stereoselectivity. The synthetic utility of this method was demonstrated by gram-scale reactions and the synthesis of key chiral intermediates for the antiasthmatic drug CP-199,330.
Article
Chemistry, Organic
Chao Zhang, You-Cai Wu, Bao-Dong Cui, Lian Li, Wen-Yong Han, Nan-Wei Wan, Yong-Zheng Chen
Summary: An organometal catalytic conversion of 3-aminooxindoles has been used for the diastereo- and enantioselective synthesis of homoallylic aminooxindoles. The application of this method offers an alternative route to build these scaffolds, with a significant conversion of products to potential applicable derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
