Literature DB >> 28910092

Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Jiajie Feng1, Michael Holmes1, Michael J Krische1.   

Abstract

Whereas numerous asymmetric methods for formation of quaternary carbon stereocenters in cyclic systems have been documented, the construction of acyclic quaternary carbon stereocenters with control of absolute stereochemistry remains a formidable challenge. This Review summarizes enantioselective methods for the construction of acyclic quaternary carbon stereocenters from achiral or chiral racemic reactants via transition metal catalysis.

Entities:  

Year:  2017        PMID： 28910092      PMCID： PMC5651685          DOI： 10.1021/acs.chemrev.7b00385

Source DB:  PubMed          Journal:  Chem Rev        ISSN： 0009-2665            Impact factor:   60.622


  120 in total

1.  Catalytic enantioselective reductive desymmetrisation of achiral and meso compounds.

Authors:  Héctor Fernández-Pérez; Pablo Etayo; Joan R Lao; José L Núñez-Rico; Anton Vidal-Ferran
Journal:  Chem Commun (Camb)       Date:  2013-11-25       Impact factor: 6.222

2.  Direct asymmetric α-allylation of aldehydes with simple allylic alcohols enabled by the concerted action of three different catalysts.

Authors:  Gaoxi Jiang; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-13       Impact factor: 15.336

3.  Bidentate hydroxyalkyl NHC ligands for the copper-catalyzed asymmetric allylic substitution of allyl phosphates with Grignard reagents.

Authors:  Magaly Magrez; Yann Le Guen; Olivier Baslé; Christophe Crévisy; Marc Mauduit
Journal:  Chemistry       Date:  2012-12-19       Impact factor: 5.236

4.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

5.  Enantioselective Rhodium-Catalyzed Allylic Alkylation of Prochiral α,α-Disubstituted Aldehyde Enolates for the Construction of Acyclic Quaternary Stereogenic Centers.

Authors:  Timothy B Wright; P Andrew Evans
Journal:  J Am Chem Soc       Date:  2016-11-18       Impact factor: 15.419

6.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

7.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

8.  Catalytic asymmetric functionalization of aromatic C-H bonds by electrophilic trapping of metal-carbene-induced zwitterionic intermediates.

Authors:  Shikun Jia; Dong Xing; Dan Zhang; Wenhao Hu
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

9.  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

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
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  46 in total

1.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

2.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

3.  Cu-Catalyzed Diastereo- and Enantioselective Reactions of γ,γ-Disubstituted Allyldiboron Compounds with Ketones.

Authors:  Joseph M Zanghi; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

4.  Diastereo- and Enantioselective Synthesis of Homoallylic Amines Bearing Quaternary Carbon Centers.

Authors:  Jacob C Green; Joseph M Zanghi; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-01-17       Impact factor: 15.419

5.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

Review 6.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

7.  Diastereo-, Enantio-, and anti-Selective Formation of Secondary Alcohol and Quaternary Carbon Stereocenters by Cu-Catalyzed Additions of B-Substituted Allyl Nucleophiles to Carbonyls.

Authors:  Emilie Wheatley; Joseph M Zanghi; Simon J Meek
Journal:  Org Lett       Date:  2020-11-18       Impact factor: 6.005

8.  Stereoselective α-Tertiary Alkylation of N-(Arylacetyl)oxazolidinones.

Authors:  Eunjae Shim; Armen Zakarian
Journal:  Synlett       Date:  2020-04       Impact factor: 2.454

9.  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

10.  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
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