Literature DB >> 25431180

Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

Kegong Ji1, Zhitong Zheng, Zhixun Wang, Liming Zhang.   

Abstract

A newly developed n class="Chemical">P,N-bidentate ligand enables enantioselective inpan>tramolecular cyclopropanation by a reactive α-oxo gold n class="Chemical">carbene intermediate generated in situ. The ligand design is based on our previously proposed structure (with a well-organized triscoordinated gold center) of the carbene intermediate in the presence of a P,N-bidentate ligand. A C2-symmetric piperidine ring was incorporated in the ligand as the nitrogen-containing moiety. A range of racemic transformations of α-oxo gold carbene intermediates have been developed recently, and this new class of chiral ligands could enable their modification for asymmetric synthesis, as demonstrated in this study.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; carbenes; cyclopropanation; gold; oxidation

Mesh:

Substances:

Year:  2014        PMID: 25431180      PMCID: PMC4300284          DOI: 10.1002/anie.201409300

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


  49 in total

1.  Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants.

Authors:  Dhananjayan Vasu; Hsiao-Hua Hung; Sabyasachi Bhunia; Sagar Ashok Gawade; Arindam Das; Rai-Shung Liu
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-06       Impact factor: 15.336

2.  LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors.

Authors:  D D Schoepp; B G Johnson; R A Wright; C R Salhoff; N G Mayne; S Wu; S L Cockerman; J P Burnett; R Belegaje; D Bleakman; J A Monn
Journal:  Neuropharmacology       Date:  1997-01       Impact factor: 5.250

3.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

4.  LY354740, a group II metabotropic glutamate receptor agonist with potential antiparkinsonian properties in rats.

Authors:  J Konieczny; K Ossowska; S Wolfarth; A Pilc
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  1998-10       Impact factor: 3.000

5.  Synthesis, in vitro pharmacology, structure-activity relationships, and pharmacokinetics of 3-alkoxy-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as potent and selective group II metabotropic glutamate receptor antagonists.

Authors:  Atsuro Nakazato; Kazunari Sakagami; Akito Yasuhara; Hiroshi Ohta; Ryoko Yoshikawa; Manabu Itoh; Masato Nakamura; Shigeyuki Chaki
Journal:  J Med Chem       Date:  2004-08-26       Impact factor: 7.446

6.  Gold-catalyzed reactions between alkenyldiazo carbonyl species and acetals.

Authors:  Vinayak Vishnu Pagar; Appaso M Jadhav; Rai-Shung Liu
Journal:  J Org Chem       Date:  2013-05-14       Impact factor: 4.354

7.  Optimizing P,N-bidentate ligands for oxidative gold catalysis: efficient intermolecular trapping of α-oxo gold carbenes by carboxylic acids.

Authors:  Kegong Ji; Yulong Zhao; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-02       Impact factor: 15.336

8.  Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones.

Authors:  Guilhem Henrion; Thomas E J Chavas; Xavier Le Goff; Fabien Gagosz
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-06       Impact factor: 15.336

9.  Gold-catalyzed synthesis of glyoxals by oxidation of terminal alkynes: one-pot synthesis of quinoxalines.

Authors:  Shuai Shi; Tao Wang; Weibo Yang; Matthias Rudolph; A Stephen K Hashmi
Journal:  Chemistry       Date:  2013-04-09       Impact factor: 5.236

10.  Gold-catalyzed oxidative rearrangement of homopropargylic ether via oxonium ylide.

Authors:  Mei Xu; Tian-Tian Ren; Chuan-Ying Li
Journal:  Org Lett       Date:  2012-09-06       Impact factor: 6.005

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  14 in total

1.  Evidence for genuine hydrogen bonding in gold(I) complexes.

Authors:  Mathilde Rigoulet; Stéphane Massou; E Daiann Sosa Carrizo; Sonia Mallet-Ladeira; Abderrahmane Amgoune; Karinne Miqueu; Didier Bourissou
Journal:  Proc Natl Acad Sci U S A       Date:  2018-12-19       Impact factor: 11.205

2.  Wolff Rearrangement of Oxidatively Generated α-Oxo Gold Carbenes: An Effective Approach to Silylketenes.

Authors:  Yang Zheng; Junqi Zhang; Xinpeng Cheng; Xinfang Xu; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-18       Impact factor: 15.336

3.  Chiral Hemilabile P,N-Ligand-Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation.

Authors:  Xiaohan Ye; Chenhuan Wang; Shuyao Zhang; Qi Tang; Lukasz Wojtas; Minyong Li; Xiaodong Shi
Journal:  Chemistry       Date:  2022-05-11       Impact factor: 5.020

4.  Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis.

Authors:  Jun-Qi Zhang; Yunkui Liu; Xing-Wang Wang; Liming Zhang
Journal:  Organometallics       Date:  2019-10-28       Impact factor: 3.876

5.  A Desulfonylative Approach in Oxidative Gold Catalysis: Regiospecific Access to Donor-Substituted Acyl Gold Carbenes.

Authors:  Hongyi Chen; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-12       Impact factor: 15.336

Review 6.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

7.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

8.  Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold.

Authors:  Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
Journal:  Nat Commun       Date:  2017-11-23       Impact factor: 14.919

9.  Iminophosphanes: Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles.

Authors:  Mark K Rong; Koen van Duin; Tom van Dijk; Jeroen J M de Pater; Berth-Jan Deelman; Martin Nieger; A W Ehlers; J Chris Slootweg; Koop Lammertsma
Journal:  Organometallics       Date:  2017-02-16       Impact factor: 3.876

10.  Anatomy of gold catalysts: facts and myths.

Authors:  Beatrice Ranieri; Imma Escofet; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2015-06-09       Impact factor: 3.876

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