Literature DB >> 23208950

Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to heterocyclic acceptors.

Jeffrey C Holder1, Alexander N Marziale, Michele Gatti, Bin Mao, Brian M Stoltz.   

Abstract

Flava Flavanone: Asymmetric conjugate additions to chromones and 4-quinolones are reported utilizing a single catalyst system formed in situ from Pd(OCOCF(3))(2) and (S)-tBuPyOX. Notably, these reactions are performed in wet solvent under ambient atmosphere, and employ readily available arylboronic acids as the nucleophile, thus providing ready access to these asymmetric heterocycles (see scheme).
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 23208950      PMCID： PMC3753812          DOI： 10.1002/chem.201203643

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  15 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.  Catalytic enantioselective synthesis of flavanones and chromanones.

Authors:  Margaret M Biddle; Michael Lin; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-03-10       Impact factor: 15.419

3.  A C(2)-symmetric chiral bis-sulfoxide ligand in a rhodium-catalyzed reaction: asymmetric 1,4-addition of sodium tetraarylborates to chromenones.

Authors:  Jun Chen; Junmin Chen; Feng Lang; Xiangyang Zhang; Linfeng Cun; Jin Zhu; Jingen Deng; Jian Liao
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

4.  Asymmetric 1,4-addition of arylboronic acids to 2,3-dihydro-4-pyridones catalyzed by axially chiral NHC-Pd(II) complexes.

Authors:  Qin Xu; Rui Zhang; Tao Zhang; Min Shi
Journal:  J Org Chem       Date:  2010-06-04       Impact factor: 4.354

5.  Antitumor agents. 199. Three-dimensional quantitative structure-activity relationship study of the colchicine binding site ligands using comparative molecular field analysis.

Authors:  S X Zhang; J Feng; S C Kuo; A Brossi; E Hamel; A Tropsha; K H Lee
Journal:  J Med Chem       Date:  2000-01-27       Impact factor: 7.446

6.  Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: preparation of air-stable and catalytically active Cu-peptide complexes.

Authors:  M Kevin Brown; Sylvia J Degrado; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2005-08-19       Impact factor: 15.336

7.  Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition.

Authors:  Toshinobu Korenaga; Keigo Hayashi; Yusuke Akaki; Ryota Maenishi; Takashi Sakai
Journal:  Org Lett       Date:  2011-03-17       Impact factor: 6.005

8.  Antitumor agents. 181. Synthesis and biological evaluation of 6,7,2',3',4'-substituted-1,2,3,4-tetrahydro-2-phenyl-4-quinolones as a new class of antimitotic antitumor agents.

Authors:  Y Xia; Z Y Yang; P Xia; K F Bastow; Y Tachibana; S C Kuo; E Hamel; T Hackl; K H Lee
Journal:  J Med Chem       Date:  1998-03-26       Impact factor: 7.446

9.  Palladium-catalyzed enantioselective conjugate addition of arylboronic acids.

Authors:  Francesca Gini; Bart Hessen; Adriaan J Minnaard
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

10.  Chiral bidentate bis(n-heterocyclic carbene)-based palladium complexes bearing carboxylate ligands: highly effective catalysts for the enantioselective conjugate addition of arylboronic acids to cyclic enones.

Authors:  Tao Zhang; Min Shi
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
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  10 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.  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

3.  Discussion Addendum for: Preparation of (S)-tert-ButylPyOx and Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids.

Authors:  Stephen R Sardini; Brian M Stoltz
Journal:  Organic Synth       Date:  2021

4.  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

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.  Mechanistic analysis of an asymmetric palladium-catalyzed conjugate addition of arylboronic acids to β-substituted cyclic enones.

Authors:  Cornelia L Boeser; Jeffrey C Holder; Buck L H Taylor; K N Houk; Brian M Stoltz; Richard N Zare
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825

7.  Cu(I)-Catalyzed Alkynylation of Quinolones.

Authors:  Aitor Maestro; Sebastien Lemaire; Syuzanna R Harutyunyan
Journal:  Org Lett       Date:  2022-01-31       Impact factor: 6.005

Review 8.  Recent advances in palladium-catalysed asymmetric 1,4-additions of arylboronic acids to conjugated enones and chromones.

Authors:  Jan Bartáček; Jan Svoboda; Martin Kocúrik; Jaroslav Pochobradský; Alexander Čegan; Miloš Sedlák; Jiří Váňa
Journal:  Beilstein J Org Chem       Date:  2021-05-10       Impact factor: 2.883

9.  A catalytic, enantioselective formal synthesis of (+)-dichroanone and (+)-taiwaniaquinone H.

Authors:  Samantha E Shockley; Jeffrey C Holder; Brian M Stoltz
Journal:  Org Lett       Date:  2014-12-09       Impact factor: 6.005

10.  Catalytic Asymmetric Formal Total Synthesis of (-)-Triptophenolide and (+)-Triptolide.

Authors:  Wen-Dan Xu; Liang-Qun Li; Ming-Ming Li; Hui-Chun Geng; Hong-Bo Qin
Journal:  Nat Prod Bioprospect       Date:  2016-04-20
  10 in total

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