Literature DB >> 26853637

Synthesis of α-aminoboronic acids.

Patricia Andrés1, Gema Ballano, M Isabel Calaza, Carlos Cativiela.   

Abstract

This review describes available methods for the preparation of α-aminoboronic acids in their racemic or in their enantiopure form. Both, highly stereoselective syntheses and asymmetric procedures leading to the stereocontrolled generation of α-aminoboronic acid derivatives are included. The preparation of acyclic, carbocyclic and azacyclic α-aminoboronic acid derivatives is covered. Within each section, the different synthetic approaches have been classified according to the key bond which is formed to complete the α-aminoboronic acid skeleton.

Entities:  

Year:  2016        PMID: 26853637     DOI: 10.1039/c5cs00886g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  12 in total

1.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

2.  Radical Retrosynthesis.

Authors:  Joel M Smith; Stephen J Harwood; Phil S Baran
Journal:  Acc Chem Res       Date:  2018-08-02       Impact factor: 22.384

3.  β-Silyloxy Allylboronate Esters through an Aldehyde Borylation/Homologation Sequence.

Authors:  Gillian F Meyer; Maggie A Nistler; Andrey V Samoshin; Brennan D McManus; Taylor A Thane; Carl J Ferber; Gregory W O'Neil; Timothy B Clark
Journal:  Tetrahedron Lett       Date:  2020-05-29       Impact factor: 2.415

4.  Isonitrile-Based Multicomponent Synthesis of β-Amino Boronic Acids as β-Lactamase Inhibitors.

Authors:  Emanuele Bassini; Stefano Gazzotti; Filomena Sannio; Leonardo Lo Presti; Jacopo Sgrignani; Jean-Denis Docquier; Giovanni Grazioso; Alessandra Silvani
Journal:  Antibiotics (Basel)       Date:  2020-05-12

5.  Enantioselective Cu(I)-catalyzed borylative cyclization of enone-tethered cyclohexadienones and mechanistic insights.

Authors:  Sandip B Jadhav; Soumya Ranjan Dash; Sundaram Maurya; Jagadeesh Babu Nanubolu; Kumar Vanka; Rambabu Chegondi
Journal:  Nat Commun       Date:  2022-02-14       Impact factor: 17.694

6.  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

7.  Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach.

Authors:  Stefan P A Hinkes; Severin Kämmerer; Christian D P Klein
Journal:  Chem Sci       Date:  2020-08-21       Impact factor: 9.825

8.  Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.

Authors:  Lili Chen; Jun-Jian Shen; Qian Gao; Senmiao Xu
Journal:  Chem Sci       Date:  2018-06-12       Impact factor: 9.825

Review 9.  Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Authors:  Fabien J T Talbot; Quentin Dherbassy; Srimanta Manna; Chunling Shi; Shibo Zhang; Gareth P Howell; Gregory J P Perry; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-28       Impact factor: 15.336

10.  Unexpected chiral vicinal tetrasubstituted diamines via borylcopper-mediated homocoupling of isatin imines.

Authors:  Marco Manenti; Leonardo Lo Presti; Giorgio Molteni; Alessandra Silvani
Journal:  Beilstein J Org Chem       Date:  2022-03-10       Impact factor: 2.883

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