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Literature DB >> 30091829

Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

Jesse A Myhill¹, Liang Zhang¹, Gabriel J Lovinger¹, James P Morken¹.

Abstract

Catalytic enantioselective conjunctive cross-coupling has been developed to construct tertiary alkylboronic esters. These reactions occur with good yield and enantioselectivity for a range of substrates. Mechanistic experiments reveal aspects of the catalytic cycle that allow hindered substrates to react without significant complicating side reactions.

Entities: Chemical Disease Gene

Keywords: asymmetric catalysis; boron; cross coupling; quaternary centers

Mesh：

Substances：

Year: 2018 PMID： 30091829 PMCID： PMC6414220 DOI： 10.1002/anie.201807775

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

39 in total

1. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors: Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal: Science Date: 2016-01-01 Impact factor: 47.728

2. Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions.

Authors: Brad P Carrow; John F Hartwig
Journal: J Am Chem Soc Date: 2011-01-31 Impact factor: 15.419

3. Mechanism of palladium-catalyzed Suzuki-Miyaura reactions: multiple and antagonistic roles of anionic "bases" and their countercations.

Authors: Christian Amatore; Gaëtan Le Duc; Anny Jutand
Journal: Chemistry Date: 2013-06-20 Impact factor: 5.236

4. 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

5. Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: The missing link.

Authors: Andy A Thomas; Scott E Denmark
Journal: Science Date: 2016-04-15 Impact factor: 47.728

6. Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors: Emma K Edelstein; Sheila Namirembe; James P Morken
Journal: J Am Chem Soc Date: 2017-03-29 Impact factor: 15.419

7. Iterative approach to oligo(arylenevinylene)s containing tetrasubstituted vinylene units.

Authors: Naoki Ishida; Yasuhiro Shimamoto; Masahiro Murakami
Journal: Org Lett Date: 2010-07-16 Impact factor: 6.005

8. Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors: Kyle W Quasdorf; Larry E Overman
Journal: Nature Date: 2014-12-11 Impact factor: 49.962

9. Stereocontrolled Synthesis of Polypropionate Fragments based on a Building Block Assembly Strategy using Lithiation-Borylation Methodologies.

Authors: Alba Millán; Pablo D Grigol Martinez; Varinder K Aggarwal
Journal: Chemistry Date: 2017-12-11 Impact factor: 5.236

10. Homologation of boronic esters with lithiated epoxides for the stereocontrolled synthesis of 1,2- and 1,3-diols and 1,2,4-triols.

Authors: Emeline Vedrenne; Olov A Wallner; Maxime Vitale; Frank Schmidt; Varinder K Aggarwal
Journal: Org Lett Date: 2009-01-01 Impact factor: 6.005

16 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. Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Authors: Chunyin Law; Yan Meng; Seung Moh Koo; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2019-04-04 Impact factor: 15.336

3. Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors: Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal: J Am Chem Soc Date: 2018-11-09 Impact factor: 15.419

4. Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift.

Authors: Mark D Aparece; Chenpeng Gao; Gabriel J Lovinger; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2018-12-12 Impact factor: 15.336

5. Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors: Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2019-08-28 Impact factor: 15.336

6. Reactions of organoboron compounds enabled by catalyst-promoted metalate shifts.

Authors: Sheila Namirembe; James P Morken
Journal: Chem Soc Rev Date: 2019-07-01 Impact factor: 54.564

7. Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins.

Authors: Raphael Bigler; Kyle A Mack; Jeff Shen; Paolo Tosatti; Chong Han; Stephan Bachmann; Haiming Zhang; Michelangelo Scalone; Andreas Pfaltz; Scott E Denmark; Stefan Hildbrand; Francis Gosselin
Journal: Angew Chem Int Ed Engl Date: 2020-01-21 Impact factor: 15.336

8. Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.

Authors: Jesse A Myhill; Christopher A Wilhelmsen; Liang Zhang; James P Morken
Journal: J Am Chem Soc Date: 2018-11-06 Impact factor: 15.419

9. Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Authors: Chunyin Law; Elton Kativhu; Johnny Wang; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2020-04-15 Impact factor: 15.336

10. Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp³) Electrophiles: Reaction Development and Application to Targets of Interest.

Authors: Seung Moh Koo; Alex J Vendola; Sarah Noemi Momm; James P Morken
Journal: Org Lett Date: 2020-01-07 Impact factor: 6.005