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Literature DB >> 28625056

Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Pavel Starkov¹, Jared T Moore², Douglas C Duquette², Brian M Stoltz², Ilan Marek¹.

Abstract

We report a divergent and modular protocol for the preparation of acyclic molecular frameworks containing newly created quaternary carbon stereocenters. Central to this approach is a sequence composed of a (1) regioselective and -retentive preparation of allyloxycarbonyl-trapped fully substituted stereodefined amide enolates and of a (2) enantioselective palladium-catalyzed decarboxylative allylic alkylation reaction using a novel bisphosphine ligand.

Entities: Chemical Disease Species

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Year: 2017 PMID： 28625056 PMCID： PMC5555155 DOI： 10.1021/jacs.7b04086

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

99 in total

1. Stereoselective formation of quaternary carbon centers: alkylation of alpha,alpha-disubstituted amide enolates.

Authors: Jeffrey M Manthorpe; James L Gleason
Journal: Angew Chem Int Ed Engl Date: 2002-07-02 Impact factor: 15.336

2. Modular, Catalytic Enantioselective Construction of Quaternary Carbon Stereocenters by Sequential Cross-Coupling Reactions.

Authors: Bowman Potter; Emma K Edelstein; James P Morken
Journal: Org Lett Date: 2016-06-16 Impact factor: 6.005

3. Stereoselective Domino Carbocyclizations of γ- and δ-Cyano-N-tosylhydrazones with Alkenylboronic Acids with Formation of Two Different C(sp(3))-C(sp(2)) Bonds on a Quaternary Stereocenter.

Authors: Manuel Plaza; Carlos Valdés
Journal: J Am Chem Soc Date: 2016-09-12 Impact factor: 15.419

4. Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution.

Authors: Michael J Ardolino; James P Morken
Journal: J Am Chem Soc Date: 2014-04-29 Impact factor: 15.419

5. Unusual allylpalladium carboxylate complexes: identification of the resting state of catalytic enantioselective decarboxylative allylic alkylation reactions of ketones.

Authors: Nathaniel H Sherden; Douglas C Behenna; Scott C Virgil; Brian M Stoltz
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Stereodefined Acyclic Polysubstituted Silyl Ketene Aminals: Asymmetric Formation of Aldol Products with Quaternary Carbon Stereocenters.

Authors: Zackaria Nairoukh; Ilan Marek
Journal: Angew Chem Int Ed Engl Date: 2015-10-08 Impact factor: 15.336

7. A simple, scalable synthetic route to (+)- and (-)-pseudoephenamine.

Authors: Kevin T Mellem; Andrew G Myers
Journal: Org Lett Date: 2013-10-18 Impact factor: 6.005

8. Enantioselective synthesis of quaternary carbon stereogenic centers through copper-catalyzed conjugate additions of aryl- and alkylaluminum reagents to acyclic trisubstituted enones.

Authors: Jennifer A Dabrowski; Matthew T Villaume; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2013-06-18 Impact factor: 15.336

9. Enantioselective synthesis of α-quaternary Mannich adducts by palladium-catalyzed allylic alkylation: total synthesis of (+)-sibirinine.

Authors: Yoshitaka Numajiri; Beau P Pritchett; Koji Chiyoda; Brian M Stoltz
Journal: J Am Chem Soc Date: 2015-01-20 Impact factor: 15.419

10. Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylation.

Authors: Jiajie Feng; Victoria J Garza; Michael J Krische
Journal: J Am Chem Soc Date: 2014-06-10 Impact factor: 15.419

14 in total

1. Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones.

Authors: Remi Lavernhe; Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal: Org Lett Date: 2020-05-18 Impact factor: 6.005

2. Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors: Jiajie Feng; Michael Holmes; Michael J Krische
Journal: Chem Rev Date: 2017-09-14 Impact factor: 60.622

3. Short Enantioselective Formal Synthesis of (-)-Platencin.

Authors: Christian Defieber; Justin T Mohr; Gennadii A Grabovyi; Brian M Stoltz
Journal: Synthesis (Stuttg) Date: 2018-07-23 Impact factor: 3.157

4. Catalytic Enantioselective Synthesis of α-Difunctionalized Cyclic Sulfones.

Authors: Eleanor Bowen; Gillian Laidlaw; Bethany C Atkinson; Timur A McArdle-Ismaguilov; Vilius Franckevičius
Journal: J Org Chem Date: 2022-07-08 Impact factor: 4.198

5. Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors: Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal: J Am Chem Soc Date: 2019-01-25 Impact factor: 15.419

6. Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.

Authors: Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal: J Am Chem Soc Date: 2018-08-02 Impact factor: 15.419

7. Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres.

Authors: Cédric Hervieu; Mariia S Kirillova; Tatiana Suárez; Marco Müller; Estíbaliz Merino; Cristina Nevado
Journal: Nat Chem Date: 2021-04-08 Impact factor: 24.427