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Literature DB >> 28604006

Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

Jean-Nicolas Desrosiers¹, Jialin Wen², Sergei Tcyrulnikov³, Soumik Biswas¹, Bo Qu¹, Liana Hie, Dmitry Kurouski¹, Ling Wu¹, Nelu Grinberg¹, Nizar Haddad¹, Carl A Busacca¹, Nathan K Yee¹, Jinhua J Song¹, Neil K Garg⁴, Xumu Zhang², Marisa C Kozlowski³, Chris H Senanayake¹.

Abstract

The development of enantioselective carbon-carbon bond couplings catalyzed by nonprecious metals is highly desirable in terms of cost efficiency and sustainability. The first nickel-catalyzed enantioselective Mizoroki-Heck coupling is reported. This transformation is accomplished via mild reaction conditions, leveraging on QuinoxP* as a chiral ligand to afford oxindoles containing quaternary stereocenters. Good reactivity and selectivity are observed in the presence of various functional groups. Computational studies suggest that the oxidative addition assembles an atropisomeric intermediate responsible for the facial selectivity of the insertion step.

Entities: Chemical Disease Gene

Year: 2017 PMID： 28604006 PMCID： PMC5634709 DOI： 10.1021/acs.orglett.7b01054

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. Stereoselective, oxidative one-carbon degradation of Alkyl(dimethyl)phosphine-boranes. Synthesis Of enantiomerically enriched secondary phosphine-boranes

Authors:
Journal: J Org Chem Date: 2000-06-30 Impact factor: 4.354

2. The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors: Amy B Dounay; Larry E Overman
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

3. Mild and efficient nickel-catalyzed Heck reactions with electron-rich olefins.

Authors: Thomas M Gøgsig; Jonatan Kleimark; Sten O Nilsson Lill; Signe Korsager; Anders T Lindhardt; Per-Ola Norrby; Troels Skrydstrup
Journal: J Am Chem Soc Date: 2011-12-22 Impact factor: 15.419

4. Low-temperature heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: implications for catalytic asymmetric heck reactions.

Authors: Andre J B Lapierre; Steven J Geib; Dennis P Curran
Journal: J Am Chem Soc Date: 2007-01-24 Impact factor: 15.419

5. Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions.

Authors: Jean-Nicolas Desrosiers; Liana Hie; Soumik Biswas; Olga V Zatolochnaya; Sonia Rodriguez; Heewon Lee; Nelu Grinberg; Nizar Haddad; Nathan K Yee; Neil K Garg; Chris H Senanayake
Journal: Angew Chem Int Ed Engl Date: 2016-09-07 Impact factor: 15.336

6. Nickel(0)-catalyzed Heck cross-coupling via activation of aryl C-OPiv bonds.

Authors: Andrew R Ehle; Qi Zhou; Mary P Watson
Journal: Org Lett Date: 2012-02-15 Impact factor: 6.005

7. Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular heck reactions.

Authors: Amy B Dounay; Keiko Hatanaka; Jeremy J Kodanko; Martin Oestreich; Larry E Overman; Lance A Pfeifer; Matthew M Weiss
Journal: J Am Chem Soc Date: 2003-05-21 Impact factor: 15.419

4. Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Authors: Shuai Yang; Yanghui Zhang
Journal: Molecules Date: 2021-12-10 Impact factor: 4.411

4 in total

Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

1. Stereoselective, oxidative one-carbon degradation of Alkyl(dimethyl)phosphine-boranes. Synthesis Of enantiomerically enriched secondary phosphine-boranes

2. The asymmetric intramolecular Heck reaction in natural product total synthesis.

3. Mild and efficient nickel-catalyzed Heck reactions with electron-rich olefins.

4. Low-temperature heck reactions of axially chiral o-iodoacrylanilides occur with chirality transfer: implications for catalytic asymmetric heck reactions.

5. Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions.

6. Nickel(0)-catalyzed Heck cross-coupling via activation of aryl C-OPiv bonds.

7. Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular heck reactions.

Review 8. Recent advances in homogeneous nickel catalysis.

9. Enantiospecific intramolecular Heck reactions of secondary benzylic ethers.

10. Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles.

1. Cu-Catalyzed Asymmetric Aminoboration of E-Vinylarenes with ^pivZPhos as the Ligand.

2. Direct amidation of non-activated phenylacetic acid and benzylamine derivatives catalysed by NiCl₂.

3. Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes.

4. Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.