Chiral Silver Complex-Catalyzed Asymmetric Conjugate Addition of 1-Pyrroline-5-Carbonitrile to α-Enones DOI
Haruna Araki,

Shohei Furuya,

Kazuya Kanemoto

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 924 - 932

Published: Jan. 10, 2023

The conjugated addition reaction of 1-pyrroline-5-carbonitrile to α-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether the presence 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and nearly single diastereomers adducts with good enantiomeric excesses (up 97% ee) were obtained high yields. reduction nitrile group H2/Raney Ni ethanol successfully transformed conjugate adduct corresponding spirocyclic piperidine (60% yield) as a stereoisomer.

Language: Английский

Synergistic Dual Catalysis in Stereodivergent Synthesis DOI
Liang Wei, Cong Fu,

Zuo-Fei Wang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(6), P. 3812 - 3844

Published: Feb. 23, 2024

Chiral skeletons with multiple stereogenic centers widely reside in nature and drugs, their relative absolute configuration often determine physiological or pharmacological properties. Stereodivergent synthesis of chiral molecules is not only great significance, but also highly challenging since the formation one diastereomers inherently preferred most asymmetric reactions. dual catalysis, introduced 2013 by Carreira group, perfectly catered to all requirements for full stereoselectivity control given reactions two catalysts are utilized a synergistic way act independently, has now been arguably efficient strategy realize stereodivergent synthesis. This comprehensive review presents an overview development enabled catalysis past ten years, providing readers fundamental attributes as well ability, scope, mechanism, limitations this strategy.

Language: Английский

Citations

36
Asymmetric transformations enabled by synergistic dual transition-metal catalysis DOI Creative Commons
Liang Wei, Chun‐Jiang Wang

Chem Catalysis, Journal Year: 2022, Volume and Issue: 3(1), P. 100455 - 100455

Published: Nov. 17, 2022

Language: Английский

Citations

56
Synergistic catalysis for stereocontrol of prochiral nucleophiles in palladium-catalyzed asymmetric allylic substitution DOI
Xi Wang,

Youbin Peng,

Ling Zhao

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(8), P. 2238 - 2255

Published: July 20, 2023

Language: Английский

Citations

19
Enantioselective Pd- and Cu-Catalyzed Hydrofunctionalization of Methylenecyclopropanes via a Distal C–C Bond Cleavage DOI
Jie Zhao,

Deyue Ren,

Jintao Xia

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C–C bond activation via oxidative addition transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters MCPs to produce α-allylated 2H-pyrrole derivatives. In this reaction, azomethine ylide formed by chiral copper catalyst with ketimine ester would serve as nucleophile react activated palladium catalysis. This bimetallic system exhibited broad substrate scope high regio- enantioselectivities.

Language: Английский

Citations

1
Asymmetric Synthesis of Anti‐tuberculosis‐specific Drug TBAJ‐876 through Synergistic Li/Li Catalysis DOI
Jing Li, Feng Gao, Tanveer Ahmad

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(11), P. 1319 - 1326

Published: Jan. 14, 2023

Comprehensive Summary TBAJ‐876, developed by TB Alliance, a novel anti‐tuberculosis‐specific drug, has entered Phase II clinical trials. Herein, the first asymmetric synthesis of TBAJ‐876 been realized using synergistic Li/Li catalysis with excellent yield 95% and 88 : 12 er (99.6 0.4 er, 10 1 dr after simple recrystallization). Furthermore, DFT calculations 7 Li‐NMR analysis illustrated mechanism reaction: chiral Li‐complex activates nucleophile to control stereoselectivity, while other achiral electrophile catalyze carbonyl addition reaction. Additionally, this protocol successfully carried out at 5 gram‐scale, showing its industrial potential.

Language: Английский

Citations

11
Asymmetric three-component Tsuji–Trost allylation reaction enabled by chiral aldehyde/palladium combined catalysis DOI Creative Commons
Jianhua Liu, Wen Wei,

Zhu‐Lian Wu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(26), P. 10232 - 10236

Published: Jan. 1, 2024

An asymmetric three-component allylation reaction is achieved under the promotion of chiral aldehyde/palladium combined catalysis via mixed Heck/allylation cascades.

Language: Английский

Citations

4
Stereodivergent dual catalysis in organic synthesis DOI

Hong Sun,

Yue Ma,

Guorong Xiao

et al.

Trends in Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

Language: Английский

Citations

3
Pd/Cu Catalyzed Asymmetric Allylation for Stereodivergent Synthesis of Glutamic Acid Derivatives DOI Open Access
Chaopeng Li, Yong Liu, Zhaobin Han

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

Abstract A synergistic Pd/Cu catalyst system has been developed for stereodivergent transformation of Morita‐Baylis‐Hillman (MBH) carbonates and Schiff bases derived from simple amino acids to afford a series optically active β‐branched γ‐methyleneglutamic acid derivatives with adjacent tertiary/tertiary quaternary/tertiary stereocenters in high yields (up 96 %) excellent diastereo‐ enantioselectivities (>20/1 dr >99 % ee most cases) under mild conditions. The use SKP ligand is disclosed be crucial the success transformation, particular allowing reaction proceed at low loading (0.02 mol Pd 0.08 Cu). efficiency catalysis was attributed formation intimate ion pair complex A1 , composed Pd‐phosphonium cation t ‐butoxide anion, which would facilitate subsequent deprotonation C−C coupling events. All four stereoisomers glutamic were readily prepared by permutation enantiomers. Synthetic utility methodology exemplified efficient synthesis fused pyrrolooxazolidinone three contiguous chiral centers, highlighting power asymmetric allylic alkylation MBH carbonates.

Language: Английский

Citations

3
Dual-Catalysis-Enabled Construction of Vicinal Stereogenic Centers through Diastereo- and Enantioselective Allylic Substitution DOI
Bo Su, Kai Yang, Lu Chen

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(22), P. 3365 - 3376

Published: April 15, 2024

Abstract Vicinal stereogenic centers represent prevalent structural motifs in organic synthetic chemistry, and their construction poses a longstanding challenge. Transition-metal-catalyzed asymmetric allylic substitution has become well-established enantioselective C–C bond-forming reaction. When these reactions involve prochiral nucleophile an electrophile with terminal substituent, the creation of vicinal becomes feasible. However, despite remarkable achievements having been accomplished, realizing this transformation precise control over both enantio- diastereoselectivity remains significant To address stereoselective challenges, introduction second catalyst to transition-metal-catalyzed alkylation during bond formation proven particularly fruitful. In short review, we aim highlight recent advances dual catalysis that enable diastereo- substitutions. 1 Introduction 2 Construction Stereogenic Centers by Organo Metal Dual Catalysis 2.1 Chiral Phase-Transfer Transition-Metal 2.2 Amine 2.3 NHC 2.4 Aldehyde 2.5 Lewis Base 3 3.1 Acidic Iridium 3.2 Palladium 3.3 Ruthenium 3.4 Other Advancements through Synergistic Bimetallic Enabling Asymmetric Allylic Alkylation 4 Conclusions Future Outlook

Language: Английский

Citations

2
Chiral Silver Complex-Catalyzed Asymmetric Conjugate Addition of 1-Pyrroline-5-Carbonitrile to α-Enones DOI
Haruna Araki,

Shohei Furuya,

Kazuya Kanemoto

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(2), P. 924 - 932

Published: Jan. 10, 2023

The conjugated addition reaction of 1-pyrroline-5-carbonitrile to α-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether the presence 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and nearly single diastereomers adducts with good enantiomeric excesses (up 97% ee) were obtained high yields. reduction nitrile group H2/Raney Ni ethanol successfully transformed conjugate adduct corresponding spirocyclic piperidine (60% yield) as a stereoisomer.

Language: Английский

Citations

3