Literature DB >> 15355068

Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds.

Ryo Shintani1, Kazuhito Ueyama, Ichiro Yamada, Tamio Hayashi.   

Abstract

[reaction: see text] A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to fumaric and maleic compounds has been developed. While phosphorus-based chiral ligands fail to induce high stereoselectivity, chiral norbornadiene ligands have proved to be uniquely effective to achieve high enantioselectivity in these 1,4-addition reactions.

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Year:  2004        PMID： 15355068     DOI： 10.1021/ol048421z

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


  9 in total

1.  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

2.  Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of trans-3,4-Disubstituted β-Lactones.

Authors:  Christian A Malapit; Irungu K Luvaga; Donald R Caldwell; Nicholas K Schipper; Amy R Howell
Journal:  Org Lett       Date:  2017-08-15       Impact factor: 6.005

3.  Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones.

Authors:  Jeffrey C Holder; Emmett D Goodman; Kotaro Kikushima; Michele Gatti; Alexander N Marziale; Brian M Stoltz
Journal:  Tetrahedron       Date:  2014-11-28       Impact factor: 2.457

4.  Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates.

Authors:  Cory C Bausch; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2008-01-23       Impact factor: 4.354

5.  Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Cyclic Electrophiles.

Authors:  Samantha E Shockley; Jeffrey C Holder; Brian M Stoltz
Journal:  Org Process Res Dev       Date:  2015-07-02       Impact factor: 3.317

6.  Organocatalytic asymmetric addition of malonates to unsaturated 1,4-diketones.

Authors:  Sergei Zari; Tiiu Kailas; Marina Kudrjashova; Mario Oeren; Ivar Järving; Toomas Tamm; Margus Lopp; Tõnis Kanger
Journal:  Beilstein J Org Chem       Date:  2012-09-04       Impact factor: 2.883

7.  Rh(I)-bisphosphine-catalyzed asymmetric, intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

Authors:  Claire M Filloux; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

8.  Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.

Authors:  David J Burns; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-22       Impact factor: 15.336

9.  The isomerization of allylrhodium intermediates in the rhodium-catalyzed nucleophilic allylation of cyclic imines.

Authors:  Hamish B Hepburn; Hon Wai Lam
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-09       Impact factor: 15.336
  9 in total

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