Literature DB >> 23148461

Catalytic desymmetrization of cyclohexadienes by asymmetric bromolactonization.

Kazutada Ikeuchi1, Shunsuke Ido, Satoshi Yoshimura, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima, Toshiyuki Kan.   

Abstract

Asymmetric bromolactonization of prochiral cyclohexadiene derivatives with N-bromosuccimide proceeded in the presence of (DHQD)(2)PHAL as a chiral catalyst to afford the corresponding bromolactones with up to 93% ee. This reaction was also applicable to the kinetic resolution of a racemic cyclic ene-carboxylic acid, where the starting material was recovered with high enantioselectivity.

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Year:  2012        PMID: 23148461     DOI: 10.1021/ol302908a

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


  13 in total

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2.  Formal Asymmetric Hydrobromination of Styrenes via Copper-Catalyzed 1,3-Halogen Migration.

Authors:  R J Van Hoveln; S C Schmid; M Tretbar; C T Buttke; J M Schomaker
Journal:  Chem Sci       Date:  2014-12-01       Impact factor: 9.825

Review 3.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

4.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354

5.  Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst.

Authors:  Chao Fang; Daniel H Paull; J Caleb Hethcox; Christopher R Shugrue; Stephen F Martin
Journal:  Org Lett       Date:  2012-11-30       Impact factor: 6.005

6.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419

7.  Diastereoselective Mannich reactions of pseudo-C2-symmetric glutarimide with activated imines.

Authors:  Tatsuya Ishikawa; Tomoko Kawasaki-Takasuka; Toshio Kubota; Takashi Yamazaki
Journal:  Beilstein J Org Chem       Date:  2017-11-21       Impact factor: 2.883

8.  Organocatalytic asymmetric chlorinative dearomatization of naphthols.

Authors:  Qin Yin; Shou-Guo Wang; Xiao-Wei Liang; De-Wei Gao; Jun Zheng; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-27       Impact factor: 9.825

9.  Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.

Authors:  Nastaran Salehi Marzijarani; Roozbeh Yousefi; Arvind Jaganathan; Kumar Dilip Ashtekar; James E Jackson; Babak Borhan
Journal:  Chem Sci       Date:  2018-01-02       Impact factor: 9.825

10.  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

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