Literature DB >> 26854364

Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes.

Lichao Fang1, Lu Yan1, Fredrik Haeffner1, James P Morken1.   

Abstract

Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

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Year:  2016        PMID： 26854364      PMCID： PMC4896641          DOI： 10.1021/jacs.5b13174

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


  15 in total

1.  Transition-metal-free diboration reaction by activation of diboron compounds with simple Lewis bases.

Authors:  Amadeu Bonet; Cristina Pubill-Ulldemolins; Carles Bo; Henrik Gulyás; Elena Fernández
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-17       Impact factor: 15.336

2.  Asymmetric organocatalytic diboration of alkenes.

Authors:  Amadeu Bonet; Cristina Sole; Henrik Gulyás; Elena Fernández
Journal:  Org Biomol Chem       Date:  2012-07-19       Impact factor: 3.876

Review 3.  Boron-selective reactions as powerful tools for modular synthesis of diverse complex molecules.

Authors:  Liang Xu; Shuai Zhang; Pengfei Li
Journal:  Chem Soc Rev       Date:  2015-09-22       Impact factor: 54.564

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.  Asymmetric conjugate alkenylation of enones catalyzed by chiral diols.

Authors:  T Robert Wu; J Michael Chong
Journal:  J Am Chem Soc       Date:  2007-04-03       Impact factor: 15.419

6.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

7.  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 8.  Theory of free energy and entropy in noncovalent binding.

Authors:  Huan-Xiang Zhou; Michael K Gilson
Journal:  Chem Rev       Date:  2009-09       Impact factor: 60.622

9.  Asymmetric synthesis from terminal alkenes by cascades of diboration and cross-coupling.

Authors:  Scott N Mlynarski; Christopher H Schuster; James P Morken
Journal:  Nature       Date:  2013-12-18       Impact factor: 49.962

10.  Hydroxyl-directed stereoselective diboration of alkenes.

Authors:  Thomas P Blaisdell; Thomas C Caya; Liang Zhang; Amparo Sanz-Marco; James P Morken
Journal:  J Am Chem Soc       Date:  2014-06-24       Impact factor: 15.419
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  20 in total

1.  Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors:  Yan Meng; Ziyin Kong; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

2.  1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

Authors:  Daniel Kaiser; Adam Noble; Valerio Fasano; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

3.  Enantio- and Diastereoselective Synthesis of Hydroxy Bis(boronates) via Cu-Catalyzed Tandem Borylation/1,2-Addition.

Authors:  Jacob C Green; Matthew V Joannou; Stephanie A Murray; Joseph M Zanghi; Simon J Meek
Journal:  ACS Catal       Date:  2017-05-25       Impact factor: 13.084

4.  Studies toward the Synthesis of Amphidinolide C1: Stereoselective Construction of the C(1)-C(15) Segment.

Authors:  Sheila Namirembe; Lu Yan; James P Morken
Journal:  Org Lett       Date:  2020-11-12       Impact factor: 6.005

5.  Practical, efficient, and broadly applicable synthesis of readily differentiable vicinal diboronate compounds by catalytic three-component reactions.

Authors:  Suttipol Radomkit; Zhenxing Liu; Anna Closs; Malte S Mikus; Amir H Hoveyda
Journal:  Tetrahedron       Date:  2017-05-20       Impact factor: 2.457

6.  Versatile Homoallylic Boronates by Chemo-, SN 2'-, Diastereo- and Enantioselective Catalytic Sequence of Cu-H Addition to Vinyl-B(pin)/Allylic Substitution.

Authors:  Jaehee Lee; Sebastian Torker; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-20       Impact factor: 15.336

7.  Site-Selective Mono-Oxidation of 1,2-Bis(boronates).

Authors:  Lu Yan; James P Morken
Journal:  Org Lett       Date:  2019-05-08       Impact factor: 6.005

Review 8.  Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Authors:  Elżbieta Wojaczyńska; Franz Steppeler; Dominika Iwan; Marie-Christine Scherrmann; Alberto Marra
Journal:  Molecules       Date:  2021-11-30       Impact factor: 4.411

9.  Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Authors:  Mingkai Zhang; Peilin Xu; Alex J Vendola; Christophe Allais; Anne-Marie Dechert Schmitt; Robert A Singer; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-08       Impact factor: 16.823

10.  New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

Authors:  Niankai Fu; Lu Song; Jinjian Liu; Yifan Shen; Juno C Siu; Song Lin
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419
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