Literature DB >> 20734008

Metal-catalyzed asymmetric conjugate addition reaction: formation of quaternary stereocenters.

Christine Hawner1, Alexandre Alexakis.   

Abstract

All-carbon quaternary stereocenters are ubiquitous motifs in biological products and pharmaceutical agents. However, due to sterical reasons, these centers are not always easily accessible. The metal-catalyzed conjugate addition reaction to trisubstituted conjugated substrates presents a viable methodology to create quaternary centers. In this article, different ways of activating the conjugate system towards nucleophilic addition will be described. An overview will be given on the different types of quaternary centers that are accessible through the conjugate addition reaction.

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Year:  2010        PMID： 20734008     DOI： 10.1039/c0cc02309d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  47 in total

1.  Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones: insights from computation and experiment.

Authors:  Jeffrey C Holder; Lufeng Zou; Alexander N Marziale; Peng Liu; Yu Lan; Michele Gatti; Kotaro Kikushima; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2013-09-27       Impact factor: 15.419

2.  Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones.

Authors:  Laura A Brozek; Joshua D Sieber; James P Morken
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

3.  Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters.

Authors:  Kotaro Kikushima; Jeffrey C Holder; Michele Gatti; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2011-04-15       Impact factor: 15.419

4.  Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.

Authors:  Christophe Allais; Andy S Tsai; Philippe Nuhant; William R Roush
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

5.  Alkenyl carbonyl derivatives in enantioselective redox relay Heck reactions: accessing α,β-unsaturated systems.

Authors:  Chun Zhang; Celine B Santiago; Lei Kou; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-06-04       Impact factor: 15.419

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

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

7.  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

8.  Copper-catalyzed asymmetric conjugate addition of alkylzirconium reagents to cyclic enones to form quaternary centers.

Authors:  Philippe M C Roth; Mireia Sidera; Rebecca M Maksymowicz; Stephen P Fletcher
Journal:  Nat Protoc       Date:  2013-12-12       Impact factor: 13.491

9.  Forming all-carbon quaternary stereogenic centres in acyclic systems from alkynes.

Authors:  Yury Minko; Morgane Pasco; Lukas Lercher; Mark Botoshansky; Ilan Marek
Journal:  Nature       Date:  2012-10-25       Impact factor: 49.962

10.  Preparation of (S)-tert-ButylPyOx and Palladium-catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Jeffrey C Holder; Samantha E Shockley; Mario P Wiesenfeldt; Hideki Shimizu; Brian M Stoltz
Journal:  Organic Synth       Date:  2016-03-04
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