Literature DB >> 20177638

Highly enantioselective Michael addition of cyclopentanone with chalcones via novel di-iminium mechanism.

Junfeng Wang1, Xin Wang, Zemei Ge, Tieming Cheng, Runtao Li.   

Abstract

The highly efficient asymmetric Michael addition reactions of cyclopentanone with chalcones were catalyzed by a simple and commercially available chiral 1,2-diaminocyclohexane-hexanedioic acid, and exhibited good yields (up to 92%) and excellent enantioselectivities (up to 99% ee). A new di-iminium mechanism for the reaction was proposed.

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Year:  2010        PMID： 20177638     DOI： 10.1039/b915852a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  4 in total

Review 1.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

2.  Organomediated cleavage of benzoyl group enables an efficient synthesis of 1-(6-nitropyridin-2-yl)thiourea and its application for developing 18F-labeled PET tracers.

Authors:  Junfeng Wang; Kazue Takahashi; Timothy M Shoup; Lichong Gong; Yingbo Li; Georges El Fakhri; Zhaoda Zhang; Anna-Liisa Brownell
Journal:  Bioorg Chem       Date:  2022-04-12       Impact factor: 5.307

3.  Enantioselective Michael addition of malonates to α,β-unsaturated ketones catalyzed by 1,2-diphenylethanediamine.

Authors:  Wei Wang; Ling Ye; Zhichuan Shi; Zhigang Zhao; Xuefeng Li
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

4.  Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters.

Authors:  Chang Shu; Honglei Liu; Alexandra M Z Slawin; Cameron Carpenter-Warren; Andrew D Smith
Journal:  Chem Sci       Date:  2019-10-23       Impact factor: 9.825
  4 in total

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