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Literature DB >> 26125083

Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran E and Other Targets of Interest.

Abstract

A hydroxyl functional group positioned β to a pinacol boronate can serve to direct palladium-catalyzed cross-coupling reactions. This feature can be used to control the reaction site in multiply borylated substrates and can activate boronates for reaction that would otherwise be unreactive.

Entities: Chemical Disease Gene

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Year: 2015 PMID： 26125083 PMCID： PMC4896638 DOI： 10.1021/jacs.5b05477

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

21 in total

1. Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Authors: Deidre L Sandrock; Ludivine Jean-Gérard; Cheng-yi Chen; Spencer D Dreher; Gary A Molander
Journal: J Am Chem Soc Date: 2010-11-15 Impact factor: 15.419

2. Efficient pd-catalyzed amination of heteroaryl halides.

Authors: Mark D Charles; Phillip Schultz; Stephen L Buchwald
Journal: Org Lett Date: 2005-09-01 Impact factor: 6.005

3. Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors: Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal: Org Lett Date: 2015-02-02 Impact factor: 6.005

4. 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

5. Stereospecific couplings of secondary and tertiary boronic esters.

Authors: Daniele Leonori; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2014-11-20 Impact factor: 15.336

Review 6. 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

7. Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration.

Authors: Daisuke Imao; Ben W Glasspoole; Véronique S Laberge; Cathleen M Crudden
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

8. 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

9. 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

10. Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors: Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal: J Am Chem Soc Date: 2014-09-23 Impact factor: 15.419

22 in total

1. 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

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. 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. 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

5. Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors: Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal: Nat Rev Chem Date: 2020-09-24 Impact factor: 34.035

6. 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

7. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

Authors: Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal: Chem Sci Date: 2022-05-30 Impact factor: 9.969

8. Catalytic SN2'- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis.

Authors: Ying Shi; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-02-04 Impact factor: 15.336

9. Palladium-Catalyzed Oxidative Carbocyclization-Borylation of Enallenes to Cyclobutenes.

Authors: Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal: Angew Chem Int Ed Engl Date: 2016-04-18 Impact factor: 15.336

10. Regio- and Stereoselective Homologation of 1,2-Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3-Diols and Sch 725674.

Authors: Alexander Fawcett; Dominik Nitsch; Muhammad Ali; Joseph M Bateman; Eddie L Myers; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2016-10-26 Impact factor: 15.336