Literature DB >> 26498040

Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Qiang Sha1, Hadi Arman2, Michael P Doyle2.   

Abstract

An efficient two-step protocol for the asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives in 99% ee from conveniently accessed 2,3-diketoesters has been developed.

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Year:  2016        PMID： 26498040      PMCID： PMC4679521          DOI： 10.1039/c5cc07780j

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


  48 in total

Review 1.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

2.  Trio catalysis merging enamine, brønsted Acid, and metal lewis Acid catalysis: asymmetric three-component aza-diels-alder reaction of substituted cinnamaldehydes, cyclic ketones, and arylamines.

Authors:  Yongming Deng; Siddhartha Kumar; Kraig Wheeler; Hong Wang
Journal:  Chemistry       Date:  2015-04-15       Impact factor: 5.236

3.  A practical synthesis of (S)-2-cyclohexyl-2-phenylglycolic acid via organocatalytic asymmetric construction of a tetrasubstituted carbon center.

Authors:  Osamu Tokuda; Taichi Kano; Wei-Guo Gao; Tetsuya Ikemoto; Keiji Maruoka
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

Review 4.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

5.  Expeditious synthesis of highly substituted indolizinones via a palladium-catalyzed domino sequence.

Authors:  Ikyon Kim; Kyungsun Kim
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

6.  N-heterocyclic carbene catalyzed formal [3+2] annulation reaction of enals: an efficient enantioselective access to spiro-heterocycles.

Authors:  Chang Guo; Michael Schedler; Constantin G Daniliuc; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-11       Impact factor: 15.336

7.  Arylamine-catalyzed enamine formation: cooperative catalysis with arylamines and acids.

Authors:  Yongming Deng; Lu Liu; Ryan G Sarkisian; Kraig Wheeler; Hong Wang; Zhenghu Xu
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

8.  Palladium-catalyzed insertion of α-diazocarbonyl compounds for the synthesis of cyclic amino esters.

Authors:  Ping-Xin Zhou; Zhao-Zhao Zhou; Zi-Sheng Chen; Yu-Ying Ye; Lian-Biao Zhao; Yan-Fang Yang; Xiao-Feng Xia; Jian-Yi Luo; Yong-Min Liang
Journal:  Chem Commun (Camb)       Date:  2012-12-03       Impact factor: 6.222

9.  Organocatalytic asymmetric Michael-Michael cascade for the construction of highly functionalized N-fused piperidinoindoline derivatives.

Authors:  Yong-Long Zhao; Yao Wang; Jian Cao; Yong-Min Liang; Peng-Fei Xu
Journal:  Org Lett       Date:  2014-04-15       Impact factor: 6.005

10.  A modular total synthesis of (±)-trigonoliimine C.

Authors:  B Narendraprasad Reddy; Chepuri V Ramana
Journal:  Chem Commun (Camb)       Date:  2013-10-28       Impact factor: 6.222
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