Literature DB >> 25387002

Enantiomerically enriched tris(boronates): readily accessible conjunctive reagents for asymmetric synthesis.

John R Coombs1, Liang Zhang, James P Morken.   

Abstract

The catalytic enantioselective diboration of vinyl boronate esters furnishes chiral tris(boronates) in a selective fashion. Subsequent deborylative alkylation occurs in a diastereoselective fashion, both for intermolecular and intramolecular processes.

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Year:  2014        PMID： 25387002      PMCID： PMC5539535          DOI： 10.1021/ja510081r

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


  29 in total

1.  Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors:  Christopher H Schuster; Bo Li; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

2.  Silver-catalyzed highly regioselective formal hydroboration of alkynes.

Authors:  Hiroto Yoshida; Ikuo Kageyuki; Ken Takaki
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005

3.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

4.  Asymmetric diboration of terminal alkenes with a rhodium catalyst and subsequent oxidation: enantioselective synthesis of optically active 1,2-diols.

Authors:  Kenji Toribatake; Hisao Nishiyama
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-02       Impact factor: 15.336

5.  Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors:  Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

6.  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

7.  Synthesis of alkenyl boronates from allyl-substituted aromatics using an olefin cross-metathesis protocol.

Authors:  Rémy Hemelaere; François Carreaux; Bertrand Carboni
Journal:  J Org Chem       Date:  2013-06-24       Impact factor: 4.354

8.  Scope and mechanism of the Pt-catalyzed enantioselective diboration of monosubstituted alkenes.

Authors:  John R Coombs; Fredrik Haeffner; Laura T Kliman; James P Morken
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

Review 9.  Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors:  Heather E Burks; James P Morken
Journal:  Chem Commun (Camb)       Date:  2007-08-22       Impact factor: 6.222

10.  Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach.

Authors:  Gary A Molander; Noel M Ellis
Journal:  J Org Chem       Date:  2008-08-06       Impact factor: 4.354
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  18 in total

1.  Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes: Scope, Mechanism, and Synthetic Applications.

Authors:  Simon Krautwald; Máté J Bezdek; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-03-01       Impact factor: 15.419

2.  Enantio- and Diastereoselective 1,2-Additions to α-Ketoesters with Diborylmethane and Substituted 1,1-Diborylalkanes.

Authors:  Stephanie A Murray; Jacob C Green; Sanita B Tailor; Simon J Meek
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-20       Impact factor: 15.336

3.  Enantioselective Synthesis of Nonracemic Geminal Silylboronates by Pt-Catalyzed Hydrosilylation.

Authors:  Adam A Szymaniak; Chenlong Zhang; John R Coombs; James P Morken
Journal:  ACS Catal       Date:  2018-02-23       Impact factor: 13.084

4.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

5.  Stereoselective Tandem Bis-Electrophile Couplings of Diborylmethane.

Authors:  Stephanie A Murray; Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2017-09-27       Impact factor: 15.419

6.  Synthesis of vinyl boronates from aldehydes by a practical boron-Wittig reaction.

Authors:  John R Coombs; Liang Zhang; James P Morken
Journal:  Org Lett       Date:  2015-03-23       Impact factor: 6.005

7.  α-Boryl Organometallic Reagents in Catalytic Asymmetric Synthesis.

Authors:  Chenlong Zhang; Weipeng Hu; James P Morken
Journal:  ACS Catal       Date:  2021-08-12       Impact factor: 13.700

8.  Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds.

Authors:  Marcin Odachowski; Amadeu Bonet; Stephanie Essafi; Philip Conti-Ramsden; Jeremy N Harvey; Daniele Leonori; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2016-07-22       Impact factor: 15.419

9.  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

10.  Selective uni- and bidirectional homologation of diborylmethane.

Authors:  Daniel J Blair; Damiano Tanini; Joseph M Bateman; Helen K Scott; Eddie L Myers; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2017-02-09       Impact factor: 9.825
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