Literature DB >> 20014787

Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates.

Steven R Inglis1, Esther C Y Woon, Amber L Thompson, Christopher J Schofield.   

Abstract

Methods for the deprotection of pinanediol and pinacol esters of various boronic acids via fluoroborane intermediates were evaluated. Treatment of the boronate esters with potassium hydrogen difluoride normally gives trifluoroborate salts; in the case of alpha-amido alkyl or o-amido phenyl boronate esters, aqueous workup gives difluoroboranes. Procedures for transformation of both trifluoroborates and difluoroboranes to free boronic acids are described.

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Year:  2010        PMID： 20014787     DOI： 10.1021/jo901930v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors:  Gary A Molander; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  A method for the deprotection of alkylpinacolyl boronate esters.

Authors:  Jing Sun; Michael T Perfetti; Webster L Santos
Journal:  J Org Chem       Date:  2011-04-07       Impact factor: 4.354

3.  Structure guided development of potent reversibly binding penicillin binding protein inhibitors.

Authors:  Esther C Y Woon; Astrid Zervosen; Eric Sauvage; Katie J Simmons; Matej Zivec; Steven R Inglis; Colin W G Fishwick; Stanislav Gobec; Paulette Charlier; André Luxen; Christopher J Schofield
Journal:  ACS Med Chem Lett       Date:  2011-01-11       Impact factor: 4.345

4.  Iridium-Catalyzed Allylic Amination Route to α-Aminoboronates: Illustration of the Decisive Role of Boron Substituents.

Authors:  Sabrina Touchet; François Carreaux; Gary A Molander; Bertrand Carboni; Alexandre Bouillon
Journal:  Adv Synth Catal       Date:  2011-12       Impact factor: 5.837

5.  Boronate derivatives of functionally diverse catechols: stability studies.

Authors:  Kamal Aziz Ketuly; A Hamid A Hadi
Journal:  Molecules       Date:  2010-03-31       Impact factor: 4.411

6.  Bicyclic Boronate VNRX-5133 Inhibits Metallo- and Serine-β-Lactamases.

Authors:  Alen Krajnc; Jürgen Brem; Philip Hinchliffe; Karina Calvopiña; Tharindi D Panduwawala; Pauline A Lang; Jos J A G Kamps; Jonathan M Tyrrell; Emma Widlake; Benjamin G Saward; Timothy R Walsh; James Spencer; Christopher J Schofield
Journal:  J Med Chem       Date:  2019-09-16       Impact factor: 7.446

7.  Primary trifluoroborate-iminiums enable facile access to chiral α-aminoboronic acids via Ru-catalyzed asymmetric hydrogenation and simple hydrolysis of the trifluoroborate moiety.

Authors:  Andrej Šterman; Izidor Sosič; Zdenko Časar
Journal:  Chem Sci       Date:  2022-01-26       Impact factor: 9.825

8.  Catalytic asymmetric hydrogenation of (Z)-α-dehydroamido boronate esters: direct route to alkyl-substituted α-amidoboronic esters.

Authors:  Yazhou Lou; Jun Wang; Gelin Gong; Fanfu Guan; Jiaxiang Lu; Jialin Wen; Xumu Zhang
Journal:  Chem Sci       Date:  2019-11-25       Impact factor: 9.825

9.  Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors:  Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal:  Chem Sci       Date:  2018-05-16       Impact factor: 9.825

10.  Bicyclic Boronates as Potent Inhibitors of AmpC, the Class C β-Lactamase from Escherichia coli.

Authors:  Pauline A Lang; Anete Parkova; Thomas M Leissing; Karina Calvopiña; Ricky Cain; Alen Krajnc; Tharindi D Panduwawala; Jules Philippe; Colin W G Fishwick; Peteris Trapencieris; Malcolm G P Page; Christopher J Schofield; Jürgen Brem
Journal:  Biomolecules       Date:  2020-06-12
  10 in total

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