Literature DB >> 25029483

Regio- and enantioselective Baeyer-Villiger oxidation: kinetic resolution of racemic 2-substituted cyclopentanones.

Lin Zhou1, Xiaohua Liu, Jie Ji, Yuheng Zhang, Wangbin Wu, Yangbin Liu, Lili Lin, Xiaoming Feng.   

Abstract

A kinetic resolution of racemic 2-substituted cyclopentanones via highly regio- and enantioselective Baeyer-Villiger oxidation has been successfully developed. The reaction could afford the normal 6-substituted δ-lactones in up to 98% ee and >19/1 regioselectivity. Meanwhile, the unreacted ketones were recovered in excellent ee values (up to 98%). It represents the best results of the kinetic resolution of racemic 2-substituted cyclopentanones via nonenzymic asymmetric BV oxidation.

Entities:  

Year:  2014        PMID： 25029483     DOI： 10.1021/ol501737a

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


  6 in total

Review 1.  Rearrangements of organic peroxides and related processes.

Authors:  Ivan A Yaremenko; Vera A Vil'; Dmitry V Demchuk; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2016-08-03       Impact factor: 2.883

2.  Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.

Authors:  Chang-Sheng Zhang; Ya-Ping Shao; Fu-Min Zhang; Xue Han; Xiao-Ming Zhang; Kun Zhang; Yong-Qiang Tu
Journal:  Chem Sci       Date:  2022-06-23       Impact factor: 9.969

Review 3.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

4.  Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution.

Authors:  Guangyue Li; Marc Garcia-Borràs; Maximilian J L J Fürst; Adriana Ilie; Marco W Fraaije; K N Houk; Manfred T Reetz
Journal:  J Am Chem Soc       Date:  2018-08-13       Impact factor: 15.419

5.  Biocatalytic Conversion of Cyclic Ketones Bearing α-Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium-Sized Carbocycles.

Authors:  Charlotte Morrill; Chantel Jensen; Xavier Just-Baringo; Gideon Grogan; Nicholas J Turner; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-05       Impact factor: 15.336

6.  Asymmetric Baeyer-Villiger oxidation: classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of meso-disubstituted cycloketones.

Authors:  Wangbin Wu; Weidi Cao; Linfeng Hu; Zhishan Su; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2019-06-10       Impact factor: 9.825
  6 in total

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