Literature DB >> 20221513

Efficient direct asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones catalyzed by vicinal primary-diamine salts.

Junfeng Wang1, Chao Qi, Zemei Ge, Tieming Cheng, Runtao Li.   

Abstract

The first direct organocatalytic asymmetric vinylogous Michael addition reactions of gamma-butenolides to chalcones have been developed by using chiral 1,2-diaminocyclohexane as a novel organocatalyst via a di-iminium transition state to provide syn-Michael products with good yields, high diastereoselectivities and enantioselectivities (up to 78% yield, >99 : 1 dr and 96% ee).

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Year:  2010        PMID： 20221513     DOI： 10.1039/b923925a

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


  8 in total

1.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

Review 2.  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

3.  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

4.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

5.  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

6.  Transition-metal-free regioselective C-H halogenation of imidazo[1,2-a]pyridines: sodium chlorite/bromite as the halogen source.

Authors:  Junxuan Li; Jiayi Tang; Yuanheng Wu; Qiuxing He; Yue Yu
Journal:  RSC Adv       Date:  2018-02-01       Impact factor: 4.036

Review 7.  C-H bond halogenation catalyzed or mediated by copper: an overview.

Authors:  Wenyan Hao; Yunyun Liu
Journal:  Beilstein J Org Chem       Date:  2015-11-09       Impact factor: 2.883

8.  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
  8 in total

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