Literature DB >> 28771334

Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Patrick T Bohan1, F Dean Toste1.   

Abstract

The development of a gold(III) catalyzed direct enantioconvergent 1,5-enyne cycloisomerization and kinetic resolution reaction is described. The transformation results in highly enantioenriched bicyclo[3.1.0]hexenes at all levels of conversion, with no racemization or symmetrization taking place during the course of the reaction, and simultaneously affords optically enriched 1,5-enynes. This report marks the first highly enantioselective transformation catalyzed by a well-defined cationic gold(III) catalyst and demonstrates the unique potential of gold(III) complexes in enantioselective catalysis.

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Year:  2017        PMID: 28771334      PMCID: PMC5911161          DOI: 10.1021/jacs.7b06025

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


  39 in total

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Authors:  Nicole M Deschamps; Vassil I Elitzin; Bing Liu; Mark B Mitchell; Matthew J Sharp; Elie A Tabet
Journal:  J Org Chem       Date:  2010-12-21       Impact factor: 4.354

2.  NHC-capped cyclodextrins (ICyDs): insulated metal complexes, commutable multicoordination sphere, and cavity-dependent catalysis.

Authors:  Maxime Guitet; Pinglu Zhang; Filipa Marcelo; Coralie Tugny; Jesús Jiménez-Barbero; Olivier Buriez; Christian Amatore; Virginie Mouriès-Mansuy; Jean-Philippe Goddard; Louis Fensterbank; Yongmin Zhang; Sylvain Roland; Mickaël Ménand; Matthieu Sollogoub
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-03       Impact factor: 15.336

Review 3.  Gold-Catalyzed Enantioselective Annulations.

Authors:  Yangyan Li; Wenbo Li; Junliang Zhang
Journal:  Chemistry       Date:  2016-10-10       Impact factor: 5.236

4.  Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au-arene interactions.

Authors:  Sachin Handa; LeGrande M Slaughter
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-04       Impact factor: 15.336

6.  C,O-Chelated BINOL/Gold(III) Complexes: Synthesis and Catalysis with Tunable Product Profiles.

Authors:  Jian-Fang Cui; Hok-Ming Ko; Ka-Pan Shing; Jie-Ren Deng; Nathanael Chun-Him Lai; Man-Kin Wong
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-06       Impact factor: 15.336

7.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

8.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

9.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Organometallic gold(III) compounds as catalysts for the addition of water and methanol to terminal alkynes.

Authors:  Raquel Casado; María Contel; Mariano Laguna; Pilar Romero; Sergio Sanz
Journal:  J Am Chem Soc       Date:  2003-10-01       Impact factor: 15.419

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  10 in total

1.  Homogeneous Gold Redox Chemistry: Organometallics, Catalysis, and Beyond.

Authors:  Banruo Huang; Mingyou Hu; F Dean Toste
Journal:  Trends Chem       Date:  2020-06-02

2.  Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.

Authors:  Gilmar A Brito; Woo-Ok Jung; Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

3.  Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles.

Authors:  Kai Liu; Guangyang Xu; Jiangtao Sun
Journal:  Chem Sci       Date:  2017-11-06       Impact factor: 9.825

4.  Cyclometalated gold(iii) complexes: noticeable differences between (N,C) and (P,C) ligands in migratory insertion.

Authors:  Jordi Serra; Pau Font; E Daiann Sosa Carrizo; Sonia Mallet-Ladeira; Stéphane Massou; Teodor Parella; Karinne Miqueu; Abderrahmane Amgoune; Xavi Ribas; Didier Bourissou
Journal:  Chem Sci       Date:  2018-03-26       Impact factor: 9.825

5.  Catalytic Activity of trans-Bis(pyridine)gold Complexes.

Authors:  Ann Christin Reiersølmoen; Dániel Csókás; Sigurd Øien-Ødegaard; Alan Vanderkooy; Arvind Kumar Gupta; Anna-Carin C Carlsson; Andreas Orthaber; Anne Fiksdahl; Imre Pápai; Máté Erdélyi
Journal:  J Am Chem Soc       Date:  2020-03-23       Impact factor: 15.419

6.  Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

Authors:  Dan Li; Yuling Yang; Minmin Zhang; Linqing Wang; Yingfan Xu; Dongxu Yang; Rui Wang
Journal:  Nat Commun       Date:  2020-05-22       Impact factor: 14.919

7.  Iron-Catalyzed Cycloisomerization and C-C Bond Activation to Access Non-canonical Tricyclic Cyclobutanes.

Authors:  Frederik Kramm; Franziska Ullwer; Benedict Klinnert; Min Zheng; Bernd Plietker
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823

8.  Strategies for remote enantiocontrol in chiral gold(iii) complexes applied to catalytic enantioselective γ,δ-Diels-Alder reactions.

Authors:  Jolene P Reid; Mingyou Hu; Susumu Ito; Banruo Huang; Cynthia M Hong; Hengye Xiang; Matthew S Sigman; F Dean Toste
Journal:  Chem Sci       Date:  2020-03-19       Impact factor: 9.825

9.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825

Review 10.  New-Generation Ligand Design for the Gold-Catalyzed Asymmetric Activation of Alkynes.

Authors:  Giuseppe Zuccarello; Imma Escofet; Ulysse Caniparoli; Antonio M Echavarren
Journal:  Chempluschem       Date:  2021-09       Impact factor: 2.863

  10 in total

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