Literature DB >> 19421581

Recent advances in enantioselective copper-catalyzed 1,4-addition.

Thomas Jerphagnon1, M Gabriella Pizzuti, Adriaan J Minnaard, Ben L Feringa.   

Abstract

A comprehensive overview of recent literature from 2003 concerning advances in enantioselective copper catalysed 1,4-addition of organometallic reagents to alpha,beta-unsaturated compounds is given in this critical review. About 200 ligands and catalysts are presented, with a focus on stereoselectivities, catalyst loading, ligand structure and substrate scope. A major part is devoted to trapping and tandem reactions and a variety of recent synthetic applications are used to illustrate the practicality and current state of the art of 1,4-addition of organometallic reagents. Finally several mechanistic studies are discussed (162 references).

Entities:  

Year:  2009        PMID: 19421581     DOI: 10.1039/b816853a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  13 in total

1.  Catalytic asymmetric carbon-carbon bond formation using alkenes as alkylmetal equivalents.

Authors:  Rebecca M Maksymowicz; Philippe M C Roth; Stephen P Fletcher
Journal:  Nat Chem       Date:  2012-07-15       Impact factor: 24.427

2.  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

3.  Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

Authors:  Jeannette M O'Brien; Kang-sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

Review 4.  Palladium(II)-catalyzed alkene functionalization via nucleopalladation: stereochemical pathways and enantioselective catalytic applications.

Authors:  Richard I McDonald; Guosheng Liu; Shannon S Stahl
Journal:  Chem Rev       Date:  2011-03-23       Impact factor: 60.622

5.  Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis.

Authors:  Rick C Betori; Karl A Scheidt
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.700

6.  A multicomponent Ni-, Zr-, and Cu-catalyzed strategy for enantioselective synthesis of alkenyl-substituted quaternary carbons.

Authors:  Kevin P McGrath; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-29       Impact factor: 15.336

7.  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

Review 8.  Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

Authors:  Katherine M Byrd
Journal:  Beilstein J Org Chem       Date:  2015-04-23       Impact factor: 2.883

9.  Formation of quaternary centres by copper catalysed asymmetric conjugate addition to β-substituted cyclopentenones with the aid of a quantitative structure-selectivity relationship.

Authors:  Ruchuta Ardkhean; Mike Mortimore; Robert S Paton; Stephen P Fletcher
Journal:  Chem Sci       Date:  2018-02-05       Impact factor: 9.825

10.  Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides.

Authors:  Mamen Rodríguez-Fernández; Xingchen Yan; Juan F Collados; Paul B White; Syuzanna R Harutyunyan
Journal:  J Am Chem Soc       Date:  2017-09-29       Impact factor: 15.419

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