Literature DB >> 24666363

Highly asymmetric bromocyclization of tryptophol: unexpected accelerating effect of DABCO-derived bromine complex.

Huan Liu1, Guangde Jiang, Xixian Pan, Xiaolong Wan, Yisheng Lai, Dawei Ma, Weiqing Xie.   

Abstract

Highly asymmetric bromocyclization of tryptophol by using chiral anionic phase-transfer catalyst and DABCO-derived brominating reagent is described. Optimization of the reaction conditions revealed that the reaction rate was accelerated together with improvement of enantioselectivity by addition of catalytic DABCO-derived brominating reagent. From tryptophol, 3-bromofuroindoline could be directly obtained in excellent enantioselectivities by employing this novel methodology.

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Year:  2014        PMID: 24666363     DOI: 10.1021/ol5004109

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


  4 in total

1.  Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion.

Authors:  Andrew J Neel; Anat Milo; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2016-03-11       Impact factor: 15.419

Review 2.  Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors:  Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-02       Impact factor: 15.336

3.  Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols.

Authors:  Zhigao Shen; Xixian Pan; Yisheng Lai; Jiadong Hu; Xiaolong Wan; Xiaoge Li; Hui Zhang; Weiqing Xie
Journal:  Chem Sci       Date:  2015-08-27       Impact factor: 9.825

4.  Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions.

Authors:  Mengna Tao; Youshao Tu; Yu Liu; Haihong Wu; Lu Liu; Junliang Zhang
Journal:  Chem Sci       Date:  2020-05-29       Impact factor: 9.825

  4 in total

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