Literature DB >> 25723255

Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Hosea M Nelson1, Brett D Williams1, Javier Miró1, F Dean Toste1.   

Abstract

A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.

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Year:  2015        PMID： 25723255      PMCID： PMC4564013          DOI： 10.1021/jacs.5b00344

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


  35 in total

1.  Asymmetric electrophilic fluorination using an anionic chiral phase-transfer catalyst.

Authors:  Vivek Rauniyar; Aaron D Lackner; Gregory L Hamilton; F Dean Toste
Journal:  Science       Date:  2011-12-23       Impact factor: 47.728

2.  Catalytic methodologies for the β-boration of conjugated electron deficient alkenes.

Authors:  Adam D J Calow; Andrew Whiting
Journal:  Org Biomol Chem       Date:  2012-06-21       Impact factor: 3.876

3.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

4.  A highly enantioselective Overman rearrangement through asymmetric counteranion-directed palladium catalysis.

Authors:  Gaoxi Jiang; Rajkumar Halder; Yewen Fang; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-01       Impact factor: 15.336

5.  Asymmetric counteranion-directed catalysis: concept, definition, and applications.

Authors:  Manuel Mahlau; Benjamin List
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-28       Impact factor: 15.336

6.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

7.  Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres.

Authors:  Helen K Scott; Varinder K Aggarwal
Journal:  Chemistry       Date:  2011-11-03       Impact factor: 5.236

8.  Stereoselective preparation of β-aryl-β-boronyl enoates and their copper-catalyzed enantioselective conjugate reduction.

Authors:  Jinyue Ding; Jack Chang Hung Lee; Dennis G Hall
Journal:  Org Lett       Date:  2012-08-15       Impact factor: 6.005

9.  Pt-catalyzed enantioselective diboration of terminal alkenes with B2(pin)2.

Authors:  Laura T Kliman; Scott N Mlynarski; James P Morken
Journal:  J Am Chem Soc       Date:  2009-09-23       Impact factor: 15.419

10.  Asymmetric fluorination of α-branched cyclohexanones enabled by a combination of chiral anion phase-transfer catalysis and enamine catalysis using protected amino acids.

Authors:  Xiaoyu Yang; Robert J Phipps; F Dean Toste
Journal:  J Am Chem Soc       Date:  2014-03-31       Impact factor: 15.419
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  34 in total

1.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

2.  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

3.  Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors:  Megan K Armstrong; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-04-03       Impact factor: 15.419

4.  Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.

Authors:  Manuel Orlandi; Margaret J Hilton; Eiji Yamamoto; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2017-08-30       Impact factor: 15.419

Review 5.  Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors:  Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-08       Impact factor: 15.336

6.  Catalyst Controlled Regiodivergent Arylboration of Dienes.

Authors:  Stephen R Sardini; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-07-12       Impact factor: 15.419

7.  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

8.  Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer.

Authors:  Eiji Yamamoto; Margaret J Hilton; Manuel Orlandi; Vaneet Saini; F Dean Toste; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-11-30       Impact factor: 15.419

9.  Multidimensional Correlations in Asymmetric Catalysis through Parameterization of Uncatalyzed Transition States.

Authors:  Manuel Orlandi; F Dean Toste; Matthew S Sigman
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-04       Impact factor: 15.336

10.  Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis.

Authors:  Banruo Huang; Ying He; Mark D Levin; Jaime A S Coelho; Robert G Bergman; F Dean Toste
Journal:  Adv Synth Catal       Date:  2019-09-06       Impact factor: 5.837
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