Cited by A gold-catalyzed cyclization/nucleophilic addition reaction of <i>o</i>-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

2-Activated 1,3-enynes in enantioselective synthesis DOI

Xiaoze Bao,

Jinhui Ren,

Yang Yang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(40), P. 7977 - 7986

Published: Jan. 1, 2020

2-Activated 1,3-enyne has emerged as a versatile synthetic precursor for the construction of valuable enantioenriched molecules.

Language: Английский

Citations

Diastereoselective Synthesis of Polysubstituted Spirocyclopenta[c]furans by Gold-Catalyzed Cascade Reaction DOI

Jialin Qi, Teng Qi,

Nuligonda Thirupathi

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(3), P. 692 - 695

Published: Jan. 11, 2019

With the synergistic activation of alkynyl alcohols and enones by a single gold catalyst, diverse multisubstituted spirocyclopenta[c]furans were synthesized in good to excellent yields under mild conditions. Three rings constructed efficiently one pot from easily available acyclic starting materials.

Language: Английский

Citations

Pd/GF-Phos-Catalyzed Asymmetric Three-Component Coupling Reaction to Access Chiral Diarylmethyl Alkynes DOI

Guofeng Zhao,

Yi Wu,

Haihong Wu

et al.

Journal of the American Chemical Society, Journal Year: 2021, Volume and Issue: 143(43), P. 17983 - 17988

Published: Oct. 26, 2021

Significant attention has been given in the past few years to selective transformations of N-tosylhydrazones various useful compounds. However, development enantioselective versions poses considerable challenges. Herein we report a Pd-catalyzed three-component coupling N-tosylhydrazone, aryl halide, and terminal alkyne under mild conditions utilizing novel chiral sulfinamide phosphine ligand (GF-Phos), which provides facile access diarylmethyl alkynes, are synthons organic synthesis as well exist skeleton many bioactive molecules. A pair enantiomers product could be easily prepared using same by simply changing substituents N-tosylhydrazone halide. The salient features this reaction include readily available starting materials, general substrate scope, high enantioselectivity, ease scale-up, conditions, versatile transformations.

Language: Английский

Citations

Enantioselectivity Tunable Gold‐Catalyzed Intermolecular [3 + 2] Cycloaddition of N‐Allenamides with Nitrones DOI

Bing Xu, Zhan‐Ming Zhang, Jie Han

et al.

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(12), P. 1407 - 1412

Published: Feb. 23, 2022

Comprehensive Summary A highly enantioselective gold‐catalyzed intermolecular [3 + 2] cycloaddition of N ‐allenamides with nitrones was realized by the application Ming‐Phos M6 as a chiral ligand. Both enantiomers cycloadducts opposite configuration could be obtained in high yields regio‐ and enantioselectivity employment either diastereomer The acidic N—H bond (hydrogen bonding) sulfinamide moiety pentaflurophenyl substituent (fluorine effect) may play important roles enhancement enantioselectivity, that is, is multifunctional ligand this transformation.

Language: Английский

Citations

Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Constructions of Bicyclo[3.2.1]oct-6-ene Frameworks via (4 + 3)-Cycloadditions DOI

Sudhakar Dattatray Tanpure,

Tung‐Chun Kuo,

Mu‐Jeng Cheng

et al.

ACS Catalysis, Journal Year: 2021, Volume and Issue: 12(1), P. 536 - 543

Published: Dec. 20, 2021

A one-pot construction of bicyclo[3.2.1]oct-6-ene frameworks involves gold-catalyzed (4 + 3)-cycloadditions between 2-(1-alkynyl)-2-alken-1-ones and substituted cyclopentadienes; diastereoselectivity (dr >25:1) enantioselectivity (up to 99.9% ee) are achieved with a chiral gold catalyst. Our DFT calculations suggest three-step ionic mechanism for the cycloadditions gold-containing 1,3-dipoles cyclopentadienes, in which an exo-spatial arrangement is preferable.

Language: Английский

Citations

Chiral Ligands for Au(I), Au(III), and Au(I)/Au(III) Redox Catalysis DOI

Sampoorna Mishra,

Urvashi Urvashi,

Nitin T. Patil

et al.

Israel Journal of Chemistry, Journal Year: 2022, Volume and Issue: 63(9)

Published: Aug. 29, 2022

Abstract Gold catalysis has emerged as an efficient tool for the selective functionalisation of C−C multiple bonds. Despite significant progress in this field, potential asymmetric gold not been fully explored to date. A historical retrospect on area reveals that enantioselective is based three pillars: Au(I) catalysis, Au(III) and Au(I)/Au(III) redox catalysis. Irrespective mode being operative, design new ligands crucial development gold‐catalysed organic transformations. This minireview summarizes made ligand focusing which were specially designed

Language: Английский

Citations

Bimetallic Catalytic Tandem Reaction of Acyclic Enynones: Enantioselective Access to Tetrahydrobenzofuran Derivatives DOI

Shulin Ge,

Yongyan Zhang,

Zheng Tan

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(9), P. 3551 - 3556

Published: April 14, 2020

A highly efficient enantioselective synthesis of multisubstituted tetrahydrobenzofuran derivatives with four contiguous stereocenters was established by the dual catalysis a gold(I)/chiral N,N′-dioxide-cobalt(II) complex via tandem cycloisomerization/Diels–Alder reaction 2-alkynyl-2-alkenones and electron-deficient olefins. This strategy not only featured atom economy, remarkable efficiency stereoselectivity but also highlighted further transformations furan-based products into polycyclic molecules. Moreover, possible transition-state model proposed to elucidate origin stereoselectivity.

Language: Английский

Citations

Ming‐Phos/Gold(I)‐Catalyzed Stereodivergent Synthesis of Highly Substituted Furo[3,4‐d][1,2]oxazines^† DOI

Lujia Zhou, Bing Xu,

Danting Ji

et al.

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 38(6), P. 577 - 582

Published: Feb. 26, 2020

Summary of main observation and conclusion A gold(I)‐catalyzed asymmetric intermolecular tandem [3+3]‐cyclization reaction 2‐(1‐alkynyl)‐2‐ alken‐1‐ones with nitrones has been developed by using Ming‐Phos as a chiral ligand. This method enables access to the stereodivergent synthesis highly substituted furo[3,4‐ d ][1,2]oxazines in excellent efficiency stereoselectivity (up 99% yield, ee , >20 : 1 dr).

Language: Английский

Citations

Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes DOI

Feilong Sun,

Chengxi Yang, Jie Ni

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(10), P. 4045 - 4050

Published: May 12, 2021

A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported. When appropriate bisphosphine and phosphine–phosphite ligands are applied, the same starting materials can be converted into two different enynyl nitriles with good yields high regioselectivities. The DFT calculations unveiled that structural features bring divergent alkyne insertion modes, which in turn lead to Moreover, synthetic value cyano-containing 1,3-enynes has been demonstrated several downstream transformations.

Language: Английский

Citations

Gold Catalysis and Furans: A Powerful Match for Synthetic Connections DOI

Stefano Nejrotti, Cristina Prandi

Synthesis, Journal Year: 2020, Volume and Issue: 53(06), P. 1046 - 1060

Published: Dec. 21, 2020

Abstract This review summarizes the advances made on synthesis and functionalization of furans via gold catalysis during period between 2016 2020. A separate section is dedicated to tandem gold-catalyzed furans. 1 Introduction 2 Gold-Catalyzed Synthesis Furans 2.1 Cycloisomerizations Alkynyl Cumulenyl Alcohols 2.2 Allenyl Ketones 2.3 Reactions with External Oxidants 2.4 Miscellaneous 3 Functionalization 3.1 Cycloadditions 3.2 Furan Ring Decorations 3.3 Involving Opening 4 Tandem Furans 4.1 Followed by Cycloaddition 4.2 a Gold 1,3- or 1,4-Dipole Intermolecular Annulation 4.3 Carbene Trapping 5 Conclusion

Language: Английский

Citations