Literature DB >> 25303227

Cooperative catalysis by palladium and a chiral phosphoric acid: enantioselective amination of racemic allylic alcohols.

Debasis Banerjee1, Kathrin Junge, Matthias Beller.   

Abstract

Cooperative catalysis by [Pd(dba)2] and the chiral phosphoric acid BA1 in combination with the phosphoramidite ligand L8 enabled the efficient enantioselective amination of racemic allylic alcohols with a variety of functionalized amines. This catalytic protocol is highly regio- and stereoselective (up to e.r. 96:4) and furnishes valuable chiral amines in almost quantitative yield.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic alcohols; asymmetric amination; chiral phosphoric acids; palladium; phosphoramidite ligands

Year:  2014        PMID： 25303227     DOI： 10.1002/anie.201405511

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  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

2.  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

3.  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 4.  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

5.  Palladium(0)-catalyzed asymmetric C(sp3)-H arylation using a chiral binol-derived phosphate and an achiral ligand.

Authors:  Lei Yang; Romain Melot; Markus Neuburger; Olivier Baudoin
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

6.  Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols.

Authors:  Xue-Gong Jia; Peng Guo; Jicheng Duan; Xing-Zhong Shu
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825

7.  Pd-Catalyzed Asymmetric N-Allylation of Amino Acid Esters with Exceptional Levels of Catalyst Control: Stereo-Divergent Synthesis of ProM-15 and Related Bicyclic Dipeptide Mimetics.

Authors:  Stephan Dohmen; Martin Reiher; Dominik Albat; Sema Akyol; Matthias Barone; Jörg-Martin Neudörfl; Ronald Kühne; Hans-Günther Schmalz
Journal:  Chemistry       Date:  2020-02-18       Impact factor: 5.236

8.  Exploring the Mechanism of the Palladium-Catalyzed 3-Butene-2-ol Amination Reaction: A DFT Study.

Authors:  Lingshan Lyu; Wei Feng; Siwei Yang; Huiling Liu; Xuri Huang
Journal:  Front Chem       Date:  2020-02-21       Impact factor: 5.221
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.