Literature DB >> 23734612

Pd-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols: the role of the chiral phosphoric acid in C-O bond cleavage and stereocontrol.

Zhong-Lin Tao1, Wen-Quan Zhang, Dian-Feng Chen, Arafate Adele, Liu-Zhu Gong.   

Abstract

The combination of a palladium complex with a chiral phosphoramidite ligand and a chiral phosphoric acid enables the first highly efficient asymmetric allylic alkylation of pyrazol-5-ones with allylic alcohols, affording multiply functionalized heterocyclic products in high yields with excellent enantioselectivities that would be of great potential in the synthesis of pharmaceutically interesting molecules.

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Year:  2013        PMID: 23734612     DOI: 10.1021/ja402740q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  9 in total

1.  A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

Authors:  Kun Liu; M Todd Hovey; Karl A Scheidt
Journal:  Chem Sci       Date:  2014-10-01       Impact factor: 9.825

2.  Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.

Authors:  Yernaidu Reddi; Cheng-Che Tsai; Carolina M Avila; F Dean Toste; Raghavan B Sunoj
Journal:  J Am Chem Soc       Date:  2018-12-28       Impact factor: 15.419

3.  Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.

Authors:  Cheng-Che Tsai; Christopher Sandford; Tao Wu; Buyun Chen; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

4.  Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts.

Authors:  Carolina M Avila; Jigar S Patel; Yernaidu Reddi; Masato Saito; Hosea M Nelson; Hunter P Shunatona; Matthew S Sigman; Raghavan B Sunoj; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-18       Impact factor: 15.336

Review 5.  Recent applications of chiral phosphoric acids in palladium catalysis.

Authors:  Van T Tran; Sri Krishna Nimmagadda; Mingyu Liu; Keary M Engle
Journal:  Org Biomol Chem       Date:  2020-01-07       Impact factor: 3.876

6.  Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes.

Authors:  Tuo Jiang; Teresa Bartholomeyzik; Javier Mazuela; Jochen Willersinn; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-24       Impact factor: 15.336

7.  Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel-Crafts reactions with a chiral bifunctional heterogeneous catalyst.

Authors:  Hong-Gang Cheng; Javier Miguélez; Hiroyuki Miyamura; Woo-Jin Yoo; Shū Kobayashi
Journal:  Chem Sci       Date:  2016-10-05       Impact factor: 9.825

8.  Stretchable chiral pockets for palladium-catalyzed highly chemo- and enantioselective allenylation.

Authors:  Yuchen Zhang; Xue Zhang; Shengming Ma
Journal:  Nat Commun       Date:  2021-04-23       Impact factor: 14.919

9.  Asymmetric higher-order [10 + n] cycloadditions of palladium-containing 10π-cycloaddends.

Authors:  Ao Li; Yang Gao; Jian-Bin Lu; Zhi-Chao Chen; Wei Du; Ying-Chun Chen
Journal:  Chem Sci       Date:  2022-07-15       Impact factor: 9.969

  9 in total

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