Literature DB >> 16268567

Asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones by rhodium-catalyzed 1,4-addition of arylzinc reagents in the presence of chlorotrimethylsilane.

Ryo Shintani1, Takafumi Yamagami, Takahiro Kimura, Tamio Hayashi.   

Abstract

[reaction: see text] The first catalytic asymmetric synthesis of 2-aryl-2,3-dihydro-4-quinolones has been developed by way of a rhodium-catalyzed 1,4-addition of arylzinc reagents to 4-quinolones. These 1,4-adducts can be obtained with high enantioselectivity by the use of (R)-binap as a ligand, and high yields are realized by conducting the reactions in the presence of chlorotrimethylsilane.

Entities:  

Year:  2005        PMID: 16268567     DOI: 10.1021/ol052257d

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


  8 in total

1.  Asymmetric Methods for the Synthesis of Flavanones, Chromanones, and Azaflavanones.

Authors:  Antoinette E Nibbs; Karl A Scheidt
Journal:  European J Org Chem       Date:  2011-12-09

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

Authors:  Jeffrey C Holder; Alexander N Marziale; Michele Gatti; Bin Mao; Brian M Stoltz
Journal:  Chemistry       Date:  2012-12-03       Impact factor: 5.236

3.  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

4.  Rhodium(I)-Complexes Catalyzed 1,4-Conjugate Addition of Arylzinc Chlorides to N-Boc-4-pyridone.

Authors:  Fenghai Guo; Matthew A McGilvary; Malcolm C Jeffries; Briana N Graves; Shekinah A Graham; Yuelin Wu
Journal:  Molecules       Date:  2017-05-01       Impact factor: 4.411

5.  Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors.

Authors:  Yafei Guo; Syuzanna R Harutyunyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

6.  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

7.  Enantioselective annulations for dihydroquinolones by in situ generation of azolium enolates.

Authors:  Anna Lee; Ashkaan Younai; Christopher K Price; Javier Izquierdo; Rama K Mishra; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2014-07-15       Impact factor: 15.419

8.  Electroreductive Intermolecular Coupling of 4-Quinolones with Benzophenones: Synthesis of 2-Substituted 4-Quinolones.

Authors:  Naoki Kise; Yoshie Yoshimura; Tatsuhiro Manto; Toshihiko Sakurai
Journal:  ACS Omega       Date:  2019-11-15
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.