Literature DB >> 30536546

PdII -Catalyzed Enantioselective C(sp3 )-H Activation/Cross-Coupling Reactions of Free Carboxylic Acids.

Liang Hu1, Peng-Xiang Shen1, Qian Shao1, Kai Hong1, Jennifer X Qiao2, Jin-Quan Yu1.   

Abstract

PdII -catalyzed enantioselective C(sp3 )-H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; arylation; palladium; vinylation

Year:  2019        PMID： 30536546      PMCID： PMC6641982          DOI： 10.1002/anie.201813055

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


  31 in total

1.  Stereoselective cyclopropanation reactions.

Authors:  Hélène Lebel; Jean-François Marcoux; Carmela Molinaro; André B Charette
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

Authors:  Edward Lee-Ruff; Gabriela Mladenova
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

3.  Pd(II)-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands.

Authors:  Bing-Feng Shi; Nathan Maugel; Yang-Hui Zhang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Fused indolines by palladium-catalyzed asymmetric C-C coupling involving an unactivated methylene group.

Authors:  Masafumi Nakanishi; Dmitry Katayev; Céline Besnard; E Peter Kündig
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-01       Impact factor: 15.336

5.  Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

Authors:  Masayuki Wasa; Keary M Engle; David W Lin; Eun Jeong Yoo; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

6.  Total synthesis of marine natural products without using protecting groups.

Authors:  Phil S Baran; Thomas J Maimone; Jeremy M Richter
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

7.  Enantioselective synthesis of 2-methyl indolines by palladium catalysed asymmetric C(sp3)-H activation/cyclisation.

Authors:  Saithalavi Anas; Alex Cordi; Henri B Kagan
Journal:  Chem Commun (Camb)       Date:  2011-09-19       Impact factor: 6.222

8.  A new chiral Rh(II) catalyst for enantioselective [2 + 1]-cycloaddition. mechanistic implications and applications.

Authors:  Yan Lou; Manabu Horikawa; Robin A Kloster; Natalie A Hawryluk; E J Corey
Journal:  J Am Chem Soc       Date:  2004-07-28       Impact factor: 15.419

Review 9.  Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity.

Authors:  Ramesh Giri; Bing-Feng Shi; Keary M Engle; Nathan Maugel; Jin-Quan Yu
Journal:  Chem Soc Rev       Date:  2009-10-01       Impact factor: 54.564

10.  In situ generation of zinc carbenoids from diazo compounds and zinc salts: asymmetric synthesis of 1,2,3-substituted cyclopropanes.

Authors:  Sébastien R Goudreau; André B Charette
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419
View more
  13 in total

1.  Enantio- and Diastereoswitchable C-H Arylation of Methylene Groups in Cycloalkanes.

Authors:  Michal S Andrä; Lukas Schifferer; Corina H Pollok; Christian Merten; Lukas J Gooßen; Jin-Quan Yu
Journal:  Chemistry       Date:  2019-05-27       Impact factor: 5.236

Review 2.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

3.  Palladium-Catalyzed Enantioselective β-C(sp3)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

Authors:  Erika L Lucas; Nelson Y S Lam; Zhe Zhuang; Hau Sun Sam Chan; Daniel A Strassfeld; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2022-01-25       Impact factor: 24.466

4.  From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors:  Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2020-03-31       Impact factor: 22.384

5.  Ligand-Enabled Monoselective β-C(sp3)-H Acyloxylation of Free Carboxylic Acids Using a Practical Oxidant.

Authors:  Zhe Zhuang; Alastair N Herron; Zhoulong Fan; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-03-30       Impact factor: 15.419

6.  Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant.

Authors:  Shaoqun Qian; Zi-Qi Li; Minyan Li; Steven R Wisniewski; Jennifer X Qiao; Jeremy M Richter; William R Ewing; Martin D Eastgate; Jason S Chen; Jin-Quan Yu
Journal:  Org Lett       Date:  2020-04-24       Impact factor: 6.005

7.  Synthesis of Cyclic Anhydrides via Ligand-Enabled C-H Carbonylation of Simple Aliphatic Acids.

Authors:  Zhe Zhuang; Alastair N Herron; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

8.  Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines.

Authors:  Jesus Rodrigalvarez; Luke A Reeve; Javier Miró; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2022-02-25       Impact factor: 16.383

9.  Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with O2.

Authors:  Chase A Salazar; Kaylin N Flesch; Brandon E Haines; Philip S Zhou; Djamaladdin G Musaev; Shannon S Stahl
Journal:  Science       Date:  2020-11-19       Impact factor: 47.728

10.  Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F.

Authors:  Zhe Zhuang; Alastair N Herron; Shuang Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-01-04       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.