4.7 Article

Asymmetric Dieckmann Condensation towards Spirocyclic Oxindoles Catalyzed by Amino Acid-derived Phosphonium Salts

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Review Chemistry, Applied

Recent Advances in Phosphonium Salt Catalysis

Hongxiang Li et al.

Summary: Quaternary phosphonium salts are extensively used as Lewis acid organocatalysts in organic synthesis, particularly for Mannich, Strecker, and Friedel-Crafts reactions, allowing the construction of structurally diverse and synthetically useful architectures.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Enantioselective alpha-Carbonylative Arylation for Facile Construction of Chiral Spirocyclic beta,beta '-Diketones

Ting Wu et al.

Summary: The study presents a novel enantioselective alpha-carbonylative arylation reaction for the synthesis of chiral spiro beta, beta'-diketones with high yield and good to excellent enantioselectivities. Computational analysis suggests that the transformation proceeds through reductive elimination rather than nucleophilic addition pathway.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Medicinal

Discovery of a First-In-Class Small Molecule Antagonist against the Adrenomedullin-2 Receptor: Structure-Activity Relationships and Optimization

Jean-Olivier Zirimwabagabo et al.

Summary: A systematic study on structure-activity relationships has led to the development of first-in-class AM2 receptor antagonists with therapeutically valuable properties and 1000-fold selectivity over the AM1 receptor. These results highlight the therapeutic potential of AM2 antagonists.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton-Todd Reaction

Siqiang Fang et al.

Summary: An innovative enantiodivergent organocatalytic method was developed for the synthesis of atropisomeric biaryls, inspired by a dipeptide-phosphonium salt-catalyzed Atherton-Todd reaction. The method allowed for the production of both R- and S-enantiomers with high selectivity factors, showcasing the potential of the newly synthesized O-phosphorylated biaryl diols. Mechanistic investigations revealed the crucial role of hydrogen bonding interactions between the catalysts and phosphorus molecules in asymmetric induction.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Hongkui Zhang et al.

Summary: Chiral (dihydro)furo-fused heterocycles are important structural elements in various natural products, functional materials, and pharmaceuticals. An efficient method using dipeptide-phosphonium salt catalysis has been developed to prepare structurally fused heterocyclic compounds with high yields and excellent stereoselectivities. Mechanistic studies revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of the reaction, particularly through initial ketone alpha-addition and hydrogen-bonding interactions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Stereodivergent Strategy in Structural Determination: Asymmetric Total Synthesis of Garcinol, Cambogin, and Related Analogues

Xueying Wang et al.

Summary: The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. An efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.

ORGANIC LETTERS (2021)

Review Chemistry, Organic

Stereoselective synthesis and applications of spirocyclic oxindoles

Alexander J. Boddy et al.

Summary: This review focuses on the development of new stereoselective approaches to spirocyclic oxindoles with spiro-3- to 8-membered rings, highlighting their importance in medicinal chemistry and as model compounds for enantioselective catalytic methodologies.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Organic

Strategies towards endo-type B polycyclic polyprenylated acylphloroglucinols: total synthesis of regio-hyperibone L and (+)-epi-clusianone

Liping Wang et al.

Summary: A concise and stereoselective method has been developed for the synthesis of polycyclic polyprenylated acylphloroglucinols and analogues in both racemic and asymmetric fashions. This method has been successfully applied in the total synthesis of natural products with biological activities.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Physical

Improving phase-transfer catalysis by enhancing non-covalent interactions

Inigo Iribarren et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2020)

Article Chemistry, Organic

Synthesis of 2,2-Disubstituted Spirocyclic Pyrrolidines by Intramolecular Dieckmann Condensation

Kateryna Fominova et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Bifunctional Ion Pair Catalysts from Chiral α-Amino Acids

Hongyu Wang et al.

CHINESE JOURNAL OF CHEMISTRY (2019)

Review Chemistry, Multidisciplinary

Recent Progress in Asymmetric Ion-Pairing Catalysis with Ammonium Salts

Deyun Qian et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Applied

Phosphonium Salts in Asymmetric Catalysis: A Journey in a Decade's Extensive Research Work

Ajij Golandaj et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Catalytic Enantioselective Synthesis of C1- and C2-Symmetric Spirobiindanones through Counterion-Directed Enolate C-Acylation

Benjamin F. Rahemtulla et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Organic

A new generation of chiral phase-transfer catalysts

Shiho Kaneko et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

Review Chemistry, Applied

Contemporary Asymmetric Phase Transfer Catalysis: Large-Scale Industrial Applications

Jiajing Tan et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2015)

Article Chemistry, Multidisciplinary

Enantiotopos-Selective C-H Oxygenation Catalyzed by a Supramolecular Ruthenium Complex

James R. Frost et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Discovery and Application of Doubly Quaternized Cinchona-Alkaloid-Based Phase-Transfer Catalysts

Bangping Xiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Applied

Amino Acid-Derived Phosphonium Salts-Catalyzed Michael Addition of 3-Substituted Oxindoles

Xiaoyu Wu et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Review Chemistry, Applied

Recent Advances in Asymmetric Organocatalytic Construction of 3,3′-Spirocyclic Oxindoles

Liang Hong et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Review Chemistry, Multidisciplinary

Asymmetric Ion-Pairing Catalysis

Katrien Brak et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Recent Developments in Asymmetric Phase-Transfer Reactions

Seiji Shirakawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Applied

Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position

Feng Zhou et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

Article Chemistry, Multidisciplinary

Cinchona-based phase-transfer catalysts for asymmetric synthesis

Sang-sup Jew et al.

CHEMICAL COMMUNICATIONS (2009)

Review Chemistry, Applied

Practical aspects of recent asymmetric phase-transfer, catalysis

Keiji Maruoka

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2008)

Review Chemistry, Multidisciplinary

Recent development and application of chiral phase-transfer catalysts

Takuya Hashimoto et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Recent advances in asymmetric phase-transfer catalysis

Takashi Ooi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Review Chemistry, Multidisciplinary

The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters

MJ O'Donnell

ACCOUNTS OF CHEMICAL RESEARCH (2004)

Review Chemistry, Multidisciplinary

Enantioselective amino acid synthesis by chiral phase-transfer catalysis

K Maruoka et al.

CHEMICAL REVIEWS (2003)