Literature DB >> 26800040

Enantioselective C-H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution.

Kai-Jiong Xiao1, Ling Chu1, Jin-Quan Yu2.   

Abstract

Significant progress has been made in the past decade regarding the development of enantioselective C-H activation reactions by desymmetrization. However, the requirement for the presence of two chemically identical prochiral C-H bonds represents an inherent limitation in scope. Reported is the first example of kinetic resolution by a palladium(II)-catalyzed enantioselective C-H activation and C-C bond formation, thus significantly expanding the scope of enantioselective C-H activation reactions.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; amino acids; enantioselectivity; kinetic resolution; palladium

Mesh：

Substances：

Year:  2016        PMID： 26800040      PMCID： PMC4899946          DOI： 10.1002/anie.201510808

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


  59 in total

1.  Enantioselective iron-catalysed O-H bond insertions.

Authors:  Shou-Fei Zhu; Yan Cai; Hong-Xiang Mao; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Nat Chem       Date:  2010-05-09       Impact factor: 24.427

2.  Copper-catalyzed asymmetric N-H insertion reactions: couplings of diazo compounds with carbamates to generate alpha-amino acids.

Authors:  Elaine C Lee; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2007-09-18       Impact factor: 15.419

3.  Enantioselective C-H amination using cationic ruthenium(II)-pybox catalysts.

Authors:  Erika Milczek; Nadège Boudet; Simon Blakey
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Ir(I)-catalyzed enantioselective secondary sp3 C-H bond activation of 2-(alkylamino)pyridines with alkenes.

Authors:  Shiguang Pan; Kohei Endo; Takanori Shibata
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

5.  Dirhodium tetracarboxylates derived from adamantylglycine as chiral catalysts for enantioselective C-h aminations.

Authors:  Ravisekhara P Reddy; Huw M L Davies
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

6.  Organocatalytic kinetic resolution via intramolecular aldol reactions: enantioselective synthesis of both enantiomers of chiral cyclohexenones.

Authors:  Liujuan Chen; Sanzhong Luo; Jiuyuan Li; Xin Li; Jin-Pei Cheng
Journal:  Org Biomol Chem       Date:  2010-04-01       Impact factor: 3.876

7.  Mechanistic rationalization of unusual kinetics in Pd-catalyzed C-H olefination.

Authors:  Ryan D Baxter; David Sale; Keary M Engle; Jin-Quan Yu; Donna G Blackmond
Journal:  J Am Chem Soc       Date:  2012-02-29       Impact factor: 15.419

8.  Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: synthesis of enantioenriched cyclobutanones and cyclopentenones.

Authors:  Ken Tanaka; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2003-07-09       Impact factor: 15.419

9.  Iridium-catalyzed enantioselective C-H alkylation of ferrocenes with alkenes using chiral diene ligands.

Authors:  Takanori Shibata; Tsubasa Shizuno
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-11       Impact factor: 15.336

10.  Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Science       Date:  2012-10-26       Impact factor: 47.728
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  8 in total

1.  Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling.

Authors:  Kai-Jiong Xiao; Ling Chu; Gang Chen; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-06-10       Impact factor: 15.419

Review 2.  Enantioselective C(sp3)‒H bond activation by chiral transition metal catalysts.

Authors:  Tyler G Saint-Denis; Ru-Yi Zhu; Gang Chen; Qing-Feng Wu; Jin-Quan Yu
Journal:  Science       Date:  2018-02-16       Impact factor: 47.728

3.  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

4.  Crystallographic and spectroscopic characterization of (R)-O-acetyl-mandelic acid.

Authors:  Cady Cirbes; Joseph M Tanski
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-06-10

5.  Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

Authors:  Duanyang Kong; Suna Han; Rui Wang; Meina Li; Guofu Zi; Guohua Hou
Journal:  Chem Sci       Date:  2017-04-19       Impact factor: 9.825

6.  Tailored trisubstituted chiral Cp x RhIII catalysts for kinetic resolutions of phosphinic amides.

Authors:  Y Sun; N Cramer
Journal:  Chem Sci       Date:  2018-02-05       Impact factor: 9.825

7.  Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.

Authors:  Xandro Vidal; José L Mascareñas; Moisés Gulías
Journal:  J Am Chem Soc       Date:  2019-01-22       Impact factor: 15.419

8.  Rhodium-Catalyzed Electrooxidative C-H Olefination of Benzamides.

Authors:  Yan Zhang; Julia Struwe; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-11       Impact factor: 16.823
  8 in total

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