4.7 Review

Recent development in asymmetric organocatalytic domino reactions involving 1,6-addition as a key step

Related references

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

Chiral Phosphoric Acid Catalyzed (4+1) Annulation of 3-Diazooxindoles/4-Diazooxisoquinolines with para-Quinone Methides to Access Chiral Spiro[dihydrobenzofuran-2,3′-oxindoles/2,4′-oxisoquinolines]

You-Cai Wu et al.

Summary: The study demonstrates an asymmetric (4+1) annulation catalyzed by a chiral phosphoric acid, leading to the synthesis of a range of spiro[dihydrobenzofuran-2,3 '-oxindoles/2,4 '-oxisoquinoline] derivatives with excellent stereocontrol. The protocol showcases metal-free participation with heterocyclic diazo compounds as direct nucleophiles, offering a straightforward and efficient process for accessing structurally-diverse spiro-heterocyclic compounds.

ADVANCED SYNTHESIS & CATALYSIS (2021)

Article Chemistry, Organic

Enantioselective Domino Reaction of 3-Vinylindole and p-Quinone Methides Enabled by Chiral Imidodiphosphoric Acids: Asymmetric Synthesis of Multisubstituted 3-Indolyl Cyclopenta[b]indoles

Ji-Gang Gao et al.

Summary: This study presents an enantioselective domino reaction between 3-vinylindole and p-quinone methide for the preparation of 3-indolyl cyclopenta[b]indoles containing multiple chiral centers. The cascade asymmetric process enabled by chiral imidodiphosphoric acids delivers products with excellent yields, enantioselectivities, and diastereoselectivities.

ORGANIC LETTERS (2021)

Review Chemistry, Organic

Recent developments in 1,6-addition reactions ofpara-quinone methides (p-QMs)

Jia-Yin Wang et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols

Meng Sun et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Enantioselective Catalytic [4+1]-Cyclization of ortho-Hydroxy-para-Quinone Methides with Allenoates

Katharina Zielke et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Multidisciplinary

Organocatalysis in aqueous media

Michelle P. van Der Helm et al.

NATURE REVIEWS CHEMISTRY (2019)

Article Chemistry, Applied

Catalytic Asymmetric [4+2] Cyclization of para-Quinone Methide Derivatives with 3-Alkyl-2-vinylindoles

Xiao-Li Jiang et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Review Multidisciplinary Sciences

N-Heterocyclic-Carbene-Catalyzed Domino Reactions via Two or More Activation Modes

Xiang-Yu Chen et al.

ISCIENCE (2018)

Review Chemistry, Applied

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Tanmoy Chanda et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

Review Chemistry, Multidisciplinary

Organocatalysis in Inert C-H Bond Functionalization

Yan Qin et al.

CHEMICAL REVIEWS (2017)

Article Chemistry, Applied

Spiro-Pyrrolidine-Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4-Dienals

Qing-Yun Dou et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

Article Chemistry, Multidisciplinary

Benzofulvenes in Trienamine Catalysis: Stereoselective Spiroindene Synthesis

Bjarke S. Donslund et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds

Kun Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Enantioselective formation of cyclopropane spiroindenes from benzofulvenes by phase transfer catalysis

Bjarke S. Donslund et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Enantioselective Vinylogous Organocascade Reactions

Hamish B. Hepburn et al.

CHEMICAL RECORD (2016)

Article Chemistry, Multidisciplinary

Controlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition Reactions by Organocatalysis

Pernille H. Poulsen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Oxadendralenes in asymmetric organocatalysis for the construction of tetrahydroisochromenes

Niels Hammer et al.

CHEMICAL SCIENCE (2016)

Article Chemistry, Multidisciplinary

Direct Catalytic Asymmetric Doubly Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactams to Dienones

Xiaodong Gu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Organocatalytic Asymmetric 1,6-Addition/1,4-Addition Sequence to 2,4-Dienals for the Synthesis of Chiral Chromans

Pernille H. Poulsen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Applied

Development and Scale-up of an Organocatalytic Enantioselective Process to Manufacture (S)-Pregabalin

Maria Moccia et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2015)

Article Chemistry, Multidisciplinary

Asymmetric Vinylogous Diels-Alder Reactions Catalyzed by a Chiral Phosphoric Acid

Xu Tian et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Organic

Synthesis of Cyclopropane Spirooxindoles by means of a Vinylogous Organocatalytic Cascade

Rodrigo Cesar da Silva et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Applied

Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes

Indranil Chatterjee et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

Article Chemistry, Multidisciplinary

Control of Remote Stereochemistry in the Synthesis of Spirocyclic Oxindoles: Vinylogous Organocascade Catalysis

Xu Tian et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Organocatalytic asymmetric remote aziridination of 2,4-dienals

Kim Soholm Halskov et al.

CHEMICAL COMMUNICATIONS (2013)

Review Chemistry, Multidisciplinary

Recent Advances in Organocatalytic Methods for Asymmetric C-C Bond Formation

Ulf Scheffler et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Review Chemistry, Applied

Recent Developments in Asymmetric Organocatalytic Domino Reactions

Helene Pellissier

ADVANCED SYNTHESIS & CATALYSIS (2012)

Article Chemistry, Multidisciplinary

Aminocatalytic Enantioselective 1,6 Additions of Alkyl Thiols to Cyclic Dienones: Vinylogous Iminium Ion Activation

Xu Tian et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Phase transfer catalyzed enantioselective cyclopropanation of 4-nitro-5-styrylisoxazoles

Claudia Del Fiandra et al.

CHEMICAL COMMUNICATIONS (2012)

Review Chemistry, Organic

1,6-Conjugate Addition of Nucleophiles to α,β,γ,δ-Diunsaturated Systems

Eduarda M. P. Silva et al.

SYNTHESIS-STUTTGART (2012)

Article Chemistry, Multidisciplinary

Asymmetric Organocatalytic 1,6-Conjugate Addition of Aldehydes to Dienic Sulfones

John J. Murphy et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Editorial Material Chemistry, Physical

Organocatalytic Asymmetric 1,6-Addition Reactions

Akkattu T. Biju

CHEMCATCHEM (2011)

Review Chemistry, Multidisciplinary

Conjugate addition reactions of carbon nucleophiles to electron-deficient dienes

Aurelio G. Csaky et al.

CHEMICAL SOCIETY REVIEWS (2010)

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Conjugate Addition of Nitroalkanes to 4-Nitro-5-styrylisoxazoles

Andrea Baschieri et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Multidisciplinary

Organocatalytic asymmetric 1,6-additions of β-ketoesters and glycine imine

Luca Bernardi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Review Chemistry, Multidisciplinary

Asymmetric organocatalytic domino reactions

Dieter Enders et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

Article Multidisciplinary Sciences

Control of four stereocentres in a triple cascade organocatalytic reaction

Dieter Enders et al.

NATURE (2006)

Article Chemistry, Multidisciplinary

Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes

M Marigo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Multidisciplinary

Enantioselective organo-cascade catalysis

Y Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Multidisciplinary

Catalytic asymmetric reductive Michael cyclization

JW Yang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Organic

Multicomponent synthesis of spiroisoxazolines

MFA Adamo et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

Review Chemistry, Multidisciplinary

In the golden age of organocatalysis

PI Dalko et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

Article Chemistry, Multidisciplinary

Asymmetric organocatalysis of 4+3 cycloaddition reactions

M Harmata et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2003)

Article Chemistry, Organic

A proline-catalyzed asymmetric Robinson annulation reaction

T Bui et al.

TETRAHEDRON LETTERS (2000)

Article Chemistry, Multidisciplinary

New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction

KA Ahrendt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)

Article Chemistry, Multidisciplinary

Proline-catalyzed direct asymmetric aldol reactions

B List et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)