4.5 Review

Organocatalytic Enantioselective Desymmetrization of Prochiral 2,2-Disubstituted Cyclic 1,3-Diones

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air

Hui Tan et al.

Summary: This study demonstrates a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of organic halides into esters utilizing O-2 as the oxygen source. Mechanistic studies show the oxidation of deoxy Breslow intermediate to Breslow intermediate for further transformation. This method expands the field of NHC catalysis and promotes oxygenation reactions with O-2.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Desymmetric Enantioselective Reduction of Cyclic 1,3-Diketones Catalyzed by a Recyclable P-Chiral Phosphinamide Organocatalyst

Xu-Long Qin et al.

Summary: The P-stereogenic phosphinamides have been demonstrated as powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol shows a broad substrate scope and high enantioselectivities and diastereoselectivities for the chiral cyclic 3-hydroxy ketone products. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species, which paves the way for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Desymmetrization of 1,3-Diones by Catalytic Enantioselective Condensation with Hydrazine

Binmiao Yang et al.

Summary: This method achieves an unprecedented desymmetrization of meso 1,3-diones by enantioselective intermolecular condensation, producing cyclic and acyclic keto-hydrazones with an all-carbon quaternary center in high efficiency and enantioselectivity. The compounds are versatile for preparing multifunctional building blocks and heterocycles with excellent stereoselectivity.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Review Chemistry, Organic

Thiourea-Tertiary Amine Promoted Cascade Catalysis: A Tool for Complexity Generation

Soniya Gandhi et al.

Summary: The research discusses the recent advancements in bifunctional organocatalyst promoted, relay-cascade catalysis, highlighting its potential for green synthesis. The cascade catalysis is categorized into double-, triple-, and quadruple cascades, each involving different combinations of reactions. This strategy has successfully achieved diverse polycyclic structural frameworks, showing promise for further development in greener chemistry approaches.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Cooperative NHC and Photoredox Catalysis for the Synthesis of β-Trifluoromethylated Alkyl Aryl Ketones

Qing-Yuan Meng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Organic

Advances in N-Heterocyclic Carbene Catalysis for Natural Product Synthesis

Yonglei Que et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Catalytic enantioselective domino Michael/transannular aldol reaction under bifunctional catalysis

Raquel Mato et al.

CHEMICAL COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions

Zi-Lei Xia et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines

Lingchao Cai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Carbene-Catalyzed Desymmetrization and Direct Construction of Arenes with All-Carbon Quaternary Chiral Center

Tingshun Zhu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Access to All-Carbon Spirocycles through a Carbene and Thiourea Cocatalytic Desymmetrization Cascade Reaction

Shitian Zhuo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Multidisciplinary

Chiral phosphoric acid catalysis: from numbers to insights

Rajat Maji et al.

CHEMICAL SOCIETY REVIEWS (2018)

Article Chemistry, Organic

Construction of 2-Thiabicyclo[3.3.1]nonanes by Organocatalytic Asymmetric Formal [3+3] Cycloaddition

Dhevalapally B. Ramachary et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Asymmetric Hydrogen Bonding Catalysis for the Synthesis of Dihydroquinazoline-Containing Antiviral, Letermovir

Cheol K. Chung et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Applied

Desymmetrization of Cyclopentenediones via Organocatalytic Cross-Dehydrogenative Coupling

Fabrizio Vetica et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process

Sara Cuadros et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

The Organocatalytic Approach to Enantiopure 2H- and 3H-Pyrroles: Inhibitors of the Hedgehog Signaling Pathway

Lisa Koetzner et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Organic

(Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers

Giorgos Koutoulogenis et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Catalytic Enantioselective Desymmetrization Reactions to All-Carbon Quaternary Stereocenters

Xing-Ping Zeng et al.

CHEMICAL REVIEWS (2016)

Review Chemistry, Multidisciplinary

Organocatalytic enantioselective desymmetrisation

A. Borissov et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Multidisciplinary

Enantioselective Formal C(sp2)-H Vinylation

Madhu Sudan Manna et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Organic

Asymmetric Desymmetrization of 1,3-Diketones via Intramolecular Benzoin Reaction

Yuanzhen Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Stronger Bronsted Acids: Recent Progress

Takahiko Akiyama et al.

CHEMICAL REVIEWS (2015)

Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Formal C(sp2)-H Alkylation

Madhu Sudan Manna et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes

Madhu Sudan Manna et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

The Total Synthesis of (-)-Nitidasin

Daniel T. Hog et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Multidisciplinary

Asymmetric Catalysis on the Nanoscale: The Organocatalytic Approach to Helicenes

Lisa Kötzner et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Organic

Protecting-Group-Free Total Synthesis of Aplykurodinone-1

Yu Tang et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

Review Multidisciplinary Sciences

Catalytic enantioselective synthesis of quaternary carbon stereocentres

Kyle W. Quasdorf et al.

NATURE (2014)

Article Chemistry, Multidisciplinary

Remarkable influence of secondary catalyst site on enantioselective desymmetrization of cyclopentenedione

Madhu Sudan Manna et al.

CHEMICAL SCIENCE (2014)

Article Chemistry, Multidisciplinary

Versatile Access to Chiral Indolines by Catalytic Asymmetric Fischer Indolization

Alberto Martinez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Organic

Bifunctional primary amine-thioureas in asymmetric organocatalysis

Olga V. Serdyuk et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

Review Chemistry, Physical

Catalytic Nazarov Cyclization: The State of the Art

Tulaza Vaidya et al.

CHEMCATCHEM (2011)

Article Chemistry, Organic

Total Synthesis of Cortistatins A and J

Shuji Yamashita et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Multidisciplinary

The Catalytic Asymmetric Fischer Indolization

Steffen Mueller et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Review Chemistry, Medicinal

Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions

Yoshiji Takemoto

CHEMICAL & PHARMACEUTICAL BULLETIN (2010)

Article Chemistry, Organic

The Pauson-Khand Reaction in the Synthesis of Pharmacologically Active Compounds

Joerg Habermann

CURRENT ORGANIC CHEMISTRY (2010)

Review Chemistry, Multidisciplinary

Synthesis of Cyclopentitols by Ring-Closing Approaches

Vanya B. Kurteva et al.

CHEMICAL REVIEWS (2009)

Review Chemistry, Organic

Organocatalytic Formation of Quaternary Stereocenters

Marco Bella et al.

SYNTHESIS-STUTTGART (2009)

Review Chemistry, Multidisciplinary

Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts

Stephen J. Connon

CHEMICAL COMMUNICATIONS (2008)

Article Chemistry, Multidisciplinary

Chiral Squaramide Derivatives are Excellent Hydrogen Bond Donor Catalysts

Jeremiah P. Malerich et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Review Chemistry, Multidisciplinary

Asymmetric enamine catalysis

Santanu Mukherjee et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Small-molecule H-bond donors in asymmetric catalysis

Abigail G. Doyle et al.

CHEMICAL REVIEWS (2007)

Review Chemistry, Multidisciplinary

Stronger bronsted acids

Takahiko Akiyama

CHEMICAL REVIEWS (2007)

Review Chemistry, Organic

Enantioselective catalytic formation of quaternary stereogenic centers

Pier Giorgio Cozzi et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2007)

Article Chemistry, Organic

Asymmetric aza-michael reactions catalyzed by cinchona alkaloids

Dario Perdicchia et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Review Chemistry, Applied

Recent advances in the catalytic Pauson-Khand-type reaction

Takanori Shibata

ADVANCED SYNTHESIS & CATALYSIS (2006)

Article Chemistry, Organic

Electrostatic repulsion as an additional selectivity factor in asymmetric proline catalysis

Jorly Joseph et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2006)

Review Chemistry, Multidisciplinary

Designer acids: Combined acid catalysis for asymmetric synthesis

H Yamamoto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Review Chemistry, Multidisciplinary

Enantiomeric steroids: Synthesis, physical, and biological properties

JF Biellmann

CHEMICAL REVIEWS (2003)

Review Chemistry, Organic

Construction of cyclopentyl units by ring contraction reactions

LF Silva

TETRAHEDRON (2002)

Article Chemistry, Multidisciplinary

The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions

S Bahmanyar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

Article Chemistry, Organic

Toward the total synthesis of variecolin

GA Molander et al.

ORGANIC LETTERS (2001)

Article Chemistry, Multidisciplinary

Proline-catalyzed direct asymmetric aldol reactions

B List et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)