Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[c]furans DOI
Yidong Wang, Zhan‐Ming Zhang, Feng Liu

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(20), P. 6403 - 6406

Published: Oct. 1, 2018

A highly enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3 + 2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with 3-stylindoles was achieved by using Ming-Phos as a chiral ligand. variety substituted cyclopenta[c]furans were obtained in good yields (up to 99%) excellent diastereoselectivities (>20:1) and enantioselectivities 97% ee). The salient features the present protocol include mild conditions, yields, high diastereo- enantioselectivities, readily available starting materials

Language: Английский

Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation DOI Creative Commons
Peichao Zhang, Yin-Lin Li, Jiafeng He

et al.

Nature Communications, Journal Year: 2021, Volume and Issue: 12(1)

Published: July 29, 2021

Abstract The simultaneous construction of two different chiralities via a simple operation poses considerable challenge. Herein cationic gold-catalyzed asymmetric hydroarylation ortho-alkynylaryl ferrocenes derivatives is developed, which enable the axial and planar chirality. here identified TY-Phos derived gold complex responsible for high yield, good diastereoselectivity (>20:1 dr), enantioselectivities (up to 99% ee) mild conditions. catalyst system also shows potential application in synthesis chiral biaryl compounds. cause enantioselectivity this investigated with density functional theory caculation.

Language: Английский

Citations

51

Gold(I)/Xiang-Phos-Catalyzed Asymmetric Intramolecular Cyclopropanation of Indenes and Trisubstituted Alkenes DOI
Peichao Zhang, Yidong Wang, Zhan‐Ming Zhang

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(22), P. 7049 - 7052

Published: Oct. 29, 2018

The first intramolecular enantioselective cyclopropanation of indenes and trisubstituted alkenes was accomplished by using new chiral phosphine X5 derived gold(I) complexes. This reaction is a straightforward, efficient method for constructing [5–3–6] fused-ring compounds with two vicinal all-carbon quaternary stereogenic centers, core structure shared numerous pharmacological products, bioactive compounds. salient features this transformation include high enantioselectivity (up to >98% ee), excellent yield (>97%), nice functional group tolerance.

Language: Английский

Citations

55

Palladium‐Catalyzed Enantioselective Reductive Heck Reactions: Convenient Access to 3,3‐Disubstituted 2,3‐Dihydrobenzofuran DOI
Zhan‐Ming Zhang, Bing Xu,

Yanyan Qian

et al.

Angewandte Chemie, Journal Year: 2018, Volume and Issue: 130(32), P. 10530 - 10534

Published: June 20, 2018

Abstract The first example of highly enantioselective intramolecular hydroarylation allyl aryl ethers was realized by palladium‐catalyzed reductive heck reactions utilizing a new chiral sulfinamide phosphine ligand (N‐Me‐ XuPhos ). N‐Me‐ can be easily prepared on gram scale from readily available starting materials in one‐pot synthesis approach. A series optically active 2,3‐dihydrobenzofurans bearing quaternary stereocenter were obtained good yields and with excellent enantioselectivities. practicality this reaction validated the straightforward CB2 receptor agonists. Moreover, deuterium efficiently incorporated into products.

Language: Английский

Citations

53

Gold(I)-Catalyzed Enantioselective [2+2+2] Cycloadditions: An Expedient Entry to Enantioenriched Tetrahydropyran Scaffolds DOI
Iván Varela, Hélio Faustino, Elena Dı́ez

et al.

ACS Catalysis, Journal Year: 2017, Volume and Issue: 7(4), P. 2397 - 2402

Published: Feb. 22, 2017

A straightforward and atom-economical enantioselective approach to highly substituted tetrahydropyrans is reported. The process, which consists of an intermolecular gold-catalyzed [2+2+2] cycloaddition between allenamides, alkenes, aldehydes, efficiently catalyzed by both phosphoramidite- chiral N-heterocyclic carbene-gold catalysts, occurs with complete chemoselectivity regioselectivity, moderate diastereoselectivity, very good enantioselectivities.

Language: Английский

Citations

52

Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[c]furans DOI
Yidong Wang, Zhan‐Ming Zhang, Feng Liu

et al.

Organic Letters, Journal Year: 2018, Volume and Issue: 20(20), P. 6403 - 6406

Published: Oct. 1, 2018

A highly enantioselective gold(I)-catalyzed intermolecular tandem cyclization/[3 + 2] cycloaddition of 2-(1-alkynyl)-2-alken-1-ones with 3-stylindoles was achieved by using Ming-Phos as a chiral ligand. variety substituted cyclopenta[c]furans were obtained in good yields (up to 99%) excellent diastereoselectivities (>20:1) and enantioselectivities 97% ee). The salient features the present protocol include mild conditions, yields, high diastereo- enantioselectivities, readily available starting materials

Language: Английский

Citations

47