Literature DB >> 25341700

Highly enantioselective one-pot synthesis of chiral β-hydroxy sulfones via asymmetric transfer hydrogenation in an aqueous medium.

Dacheng Zhang1, Tanyu Cheng, Qiankun Zhao, Jianyou Xu, Guohua Liu.   

Abstract

A mild transformation in an aqueous medium for the one-pot synthesis of optically active β-hydroxy sulfones is described. The intermediates of β-keto sulfones obtained via a nucleophilic substitution reaction of α-bromoketones and sodium sulfinates in H2O/MeOH (1:3, v/v) at 50 °C were reduced through Ru-catalyzed asymmetric transfer hydrogenation in one-pot using HCOONa as a hydrogen source providing a variety of chiral β-hydroxy sulfones with high yields and excellent enantioselectivities.

Entities:  

Year:  2014        PMID: 25341700     DOI: 10.1021/ol502832a

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


  3 in total

Review 1.  Synthesis and applications of sodium sulfinates (RSO2Na): a powerful building block for the synthesis of organosulfur compounds.

Authors:  Raju Jannapu Reddy; Arram Haritha Kumari
Journal:  RSC Adv       Date:  2021-03-01       Impact factor: 3.361

2.  Chemoenzymatic Oxosulfonylation-Bioreduction Sequence for the Stereoselective Synthesis of β-Hydroxy Sulfones.

Authors:  Marina López-Agudo; Nicolás Ríos-Lombardía; Javier González-Sabín; Iván Lavandera; Vicente Gotor-Fernández
Journal:  ChemSusChem       Date:  2021-08-19       Impact factor: 9.140

3.  Sulfone Group as a Versatile and Removable Directing Group for Asymmetric Transfer Hydrogenation of Ketones.

Authors:  Vijyesh K Vyas; Guy J Clarkson; Martin Wills
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-01       Impact factor: 15.336

  3 in total

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