Literature DB >> 22893545

An asymmetric aerobic aza-Wacker-type cyclization: synthesis of isoindolinones bearing tetrasubstituted carbon stereocenters.

Guoqiang Yang1, Chaoren Shen, Wanbin Zhang.   

Abstract

It's all in the solvent: An enantioselective variant of an aza-Wacker-type cyclization that gives isoindolinones containing tetrasubstituted carbon centers α to the nitrogen atom has been developed (see scheme; tfa=trifluoroacetate). The use of a highly coordinating solvent is crucial for the activity of the catalyst and the stereoselectivity the reaction (up to 99 % ee).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 22893545     DOI: 10.1002/anie.201203693

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  12 in total

1.  Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction.

Authors:  Jamie R Allen; Ana Bahamonde; Yukino Furukawa; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

2.  Enantioselective Markovnikov Addition of Carbamates to Allylic Alcohols for the Construction of α-Secondary and α-Tertiary Amines.

Authors:  Ana Bahamonde; Buthainah Al Rifaie; Victor Martín-Heras; Jamie R Allen; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations.

Authors:  Adam B Weinstein; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

Review 5.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354

6.  Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.

Authors:  Nicholas L Reed; Grace A Lutovsky; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2021-04-15       Impact factor: 15.419

7.  The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.

Authors:  Pavel Kočovský; Jan-E Bäckvall
Journal:  Chemistry       Date:  2014-11-05       Impact factor: 5.236

8.  A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen.

Authors:  Hu Li; Hongguo Wu; Heng Zhang; Yaqiong Su; Song Yang; Emiel J M Hensen
Journal:  ChemSusChem       Date:  2019-07-17       Impact factor: 8.928

9.  Chiral Phase Transfer Catalysis in the Asymmetric Synthesis of a 3,3-Disubstituted Isoindolinone and Determination of Its Absolute Configuration by VCD Spectroscopy.

Authors:  Guglielmo Monaco; Maximilian Tiffner; Antonia Di Mola; Wouter Herrebout; Mario Waser; Antonio Massa
Journal:  Molecules       Date:  2020-05-12       Impact factor: 4.411

10.  Bifunctional phase-transfer catalysis in the asymmetric synthesis of biologically active isoindolinones.

Authors:  Antonia Di Mola; Maximilian Tiffner; Francesco Scorzelli; Laura Palombi; Rosanna Filosa; Paolo De Caprariis; Mario Waser; Antonio Massa
Journal:  Beilstein J Org Chem       Date:  2015-12-15       Impact factor: 2.883

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