O-Allylhydroxyamine: a Bifunctional Olefin for Construction of Axially and Centrally Chiral Amino Alcohols via Asymmetric Carboamidation DOI Open Access
Jiahao Chen, Bing‐Feng Shi

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(6), P. 2252 - 2252

Published: Jan. 1, 2023

Language: Английский

Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight DOI

Haifang Meng,

Huiying Xu, Zhi Zhou

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(18), P. 7012 - 7021

Published: Jan. 1, 2022

A robust and convenient rhodium-catalyzed unconventionally regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones which are prevalent in natural products pharmaceuticals was developed.

Language: Английский

Citations

18

Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis DOI
Santosh K. Nanda

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11298 - 11319

Published: Jan. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Language: Английский

Citations

10

Synthesis of 2-aminobenzofurans via base-mediated [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes DOI
Kaifeng Chen, Weijie Chen, Fangyuan Chen

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4452 - 4458

Published: Jan. 1, 2021

Efficient metal-free [3 + 2] annulation of N-phenoxy amides with gem-difluoroalkenes has been realized for the assembly 2-aminobenzofuran derivatives potent cytotoxicity against cancer cell lines and application potential DELs.

Language: Английский

Citations

22

Enantioselective synthesis of indenopyrazolopyrazolones enabled by dual directing groups-assisted and rhodium(III)-catalyzed tandem C-H alkenylation/[3 + 2] stepwise cycloaddition DOI
Min Wu, Hui Gao, Huiying Xu

et al.

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(2), P. 842 - 846

Published: Aug. 8, 2021

Language: Английский

Citations

21

Rhodium-catalyzed enantio- and diastereoselective carboamidation of bicyclic olefins toward construction of remote chiral centers and axis DOI
Jinlei Wang, Xingwei Li

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 2046 - 2052

Published: June 20, 2023

Language: Английский

Citations

9

Rhodium‐Catalyzed Atroposelective Access to Axially Chiral Olefins via C−H Bond Activation and Directing Group Migration DOI

Ruijie Mi,

Haohua Chen, Xukai Zhou

et al.

Angewandte Chemie, Journal Year: 2021, Volume and Issue: 134(1)

Published: Oct. 22, 2021

Abstract Axially chiral open‐chain olefins represent an underexplored class of platform. In this report, two classes tetrasubstituted axially acyclic have been accessed in excellent enantioselectivity and regioselectivity via C−H activation (hetero)arenes assisted by a migratable directing group en route to coupling with sterically hindered alkynes. The indoles bearing N‐aminocarbonyl afforded C–N acrylamides the assistance racemic zinc carboxylate additive. DFT studies suggest β‐nitrogen elimination–reinsertion pathway for migration. Meanwhile, employment N‐phenoxycarboxamide delivered C−C enamides migration oxidizing group. Experiments that both cases (hetero)arene substrate adopts well‐defined orientation during activation, which turn determines disposition alkyne migratory insertion. Synthetic applications representative are demonstrated.

Language: Английский

Citations

20

Rh(III)-Catalyzed C–H Activation/[3 + 2] Annulation of N-Phenoxyacetamides via Carbooxygenation of 1,3-Dienes DOI

Liexin Wu,

Liping Li,

Haiman Zhang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(10), P. 3844 - 3849

Published: April 19, 2021

A unique Rh(III)-catalyzed C–H activation/[3 + 2] annulation of N-phenoxyacetamides has been developed for the construction dihydrobenzofurans via carbooxygenation 1,3-dienes. This transformation features a redox-neutral process with specific chemoselectivity, good substrate/functional group compatibility, and profound synthetic potentials. preliminary exploration to realize their asymmetric synthesis have also successfully demonstrated, which further strengthens practicality this approach.

Language: Английский

Citations

18

Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation DOI Creative Commons
Pu‐Fan Qian, Jun-Yi Li, Yibo Zhou

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 466 - 485

Published: Sept. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Language: Английский

Citations

7

SCpRh(III)-Catalyzed Asymmetric C–H Trifluoromethylalkylation of N-Methoxybenzamides with β-Trifluoromethyl-α,β-Unsaturated Ketones DOI
Zhuo Wu, Muzi Li, Qing Gu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1501 - 1505

Published: Feb. 13, 2024

Asymmetric C–H trifluoromethylalkylation represents a novel and straightforward synthetic method for the construction of chiral CF3-containing compounds. However, reported examples remain limited, given challenges reactivity enantioselective control. Herein, we report SCpRh(III)-catalyzed asymmetric aryl alkenyl reaction with β-trifluoromethyl-α,β-unsaturated ketones. The CF3-bearing adducts were obtained in moderate to good yields high enantioselectivity (up 81% yield 96% ee). features mild conditions broad substrate scope. products could undergo diverse functional group transformations.

Language: Английский

Citations

2

Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of N-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature DOI

Balu Ramesh,

Masilamani Jeganmohan

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 5713 - 5729

Published: April 12, 2022

Co(III)-catalyzed regio- and chemoselective redox-neutral C-H annulation of arylamides/acrylamides with 1,3-dienes is described. The present reaction was well suited a less-reactive 1,3-butadiene. By employing this protocol, pharmaceutically important 3,4-dihydroisoquinolinones were synthesized in good yields. Furthermore, the prepared converted into highly oxirane derivatives A plausible mechanistic cycle proposed supported by competition experiment kinetic isotopic effect (KIE) studies.

Language: Английский

Citations

10