Literature DB >> 20446712

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

Qin Xu1, Rui Zhang, Tao Zhang, Min Shi.   

Abstract

Axially chiral cis-chelated bidentate bis(N-heterocyclic carbene)-palladium(II) complexes are effective catalysts for the asymmetric conjugate addition of arylboronic acids to 2,3-dihydro-4-pyridones, producing the synthetically and biologically important 2-aryl-4-piperidones in moderate-to-high yields (up to 96%) along with excellent enantioselectivities (up to >99.5% ee) in most cases under mild conditions.

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Year:  2010        PMID: 20446712     DOI: 10.1021/jo1006224

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 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.  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

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.  Sequential aldol condensation-transition metal-catalyzed addition reactions of aldehydes, methyl ketones, and arylboronic acids.

Authors:  Yuan-Xi Liao; Chun-Hui Xing; Matthew Israel; Qiao-Sheng Hu
Journal:  Org Lett       Date:  2011-03-18       Impact factor: 6.005

5.  Catalytic Allylic Oxidation of Cyclic Enamides and 3,4-Dihydro-2H-Pyrans by TBHP.

Authors:  Yang Yu; Ranad Humeidi; James R Alleyn; Michael P Doyle
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

6.  Tandem Aldol Condensation - Platinacycle-Catalyzed Addition Reactions of Aldehydes, Methyl Ketones and Arylboronic Acids.

Authors:  Yuan-Xi Liao; Qiao-Sheng Hu
Journal:  European J Org Chem       Date:  2012-09-05

7.  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

8.  Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes.

Authors:  Adwait R Ranade; Gunda I Georg
Journal:  J Org Chem       Date:  2014-01-13       Impact factor: 4.354

Review 9.  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

10.  Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions.

Authors:  Yafei Guo; Marta Castiñeira Reis; Johanan Kootstra; Syuzanna R Harutyunyan
Journal:  ACS Catal       Date:  2021-06-28       Impact factor: 13.084

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