Literature DB >> 23461803

Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology.

Charlotte G Watson1, Varinder K Aggarwal.   

Abstract

The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.

Entities:  

Year:  2013        PMID: 23461803     DOI: 10.1021/ol400289v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Transition-Metal-Free ipso-Functionalization of Arylboronic Acids and Derivatives.

Authors:  Chen Zhu; John R Falck
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

2.  Synthesis of Chiral Tertiary Boronic Esters by Oxime-Directed Catalytic Asymmetric Hydroboration.

Authors:  Veronika M Shoba; Nathan C Thacker; Andrew J Bochat; James M Takacs
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-10       Impact factor: 15.336

3.  Small-Molecule Anti-HIV-1 Agents Based on HIV-1 Capsid Proteins.

Authors:  Takuya Kobayakawa; Masaru Yokoyama; Kohei Tsuji; Masayuki Fujino; Masaki Kurakami; Sayaka Boku; Miyuki Nakayama; Moemi Kaneko; Nami Ohashi; Osamu Kotani; Tsutomu Murakami; Hironori Sato; Hirokazu Tamamura
Journal:  Biomolecules       Date:  2021-02-03

4.  Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol.

Authors:  Stefan Roesner; Daniel J Blair; Varinder K Aggarwal
Journal:  Chem Sci       Date:  2015-04-28       Impact factor: 9.825

5.  Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance.

Authors:  Michelle A Garrison; Andrew R Mahoney; William M Wuest
Journal:  ChemMedChem       Date:  2020-10-16       Impact factor: 3.466

  5 in total

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