Literature DB >> 21650190

Highly regio- and diastereoselective construction of spirocyclopenteneoxindoles through phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman carbonates with isatylidene malononitriles.

Hong-Ping Deng1, Yin Wei, Min Shi.   

Abstract

Phosphine-catalyzed highly regio- and diastereoselective [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with isatylidene malononitriles has been disclosed to give the corresponding spirocyclopenteneoxindoles in excellent yields under mild conditions. A plausible reaction mechanism has also been proposed on the basis of previous literature.

Entities:  

Year:  2011        PMID: 21650190     DOI: 10.1021/ol201094f

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


  11 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations.

Authors:  Yumei Xiao; Hongchao Guo; Ohyun Kwon
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

3.  Catalytic, enantioselective 1,3-dipolar cycloadditions of nitrile imines with methyleneindolinones.

Authors:  Anthony L Gerten; Michael C Slade; Kelsie M Pugh; Levi M Stanley
Journal:  Org Biomol Chem       Date:  2013-10-17       Impact factor: 3.876

4.  Enantioselective one-pot synthesis of α-amino esters by a phosphine-catalyzed [3+2]-cycloaddition reaction.

Authors:  Marianne Steurer; Kim L Jensen; Dennis Worgull; Karl Anker Jørgensen
Journal:  Chemistry       Date:  2011-12-07       Impact factor: 5.236

5.  Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3 + 2] annulation of Morita-Baylis-Hillman carbonates with maleimides.

Authors:  Hong-Ping Deng; De Wang; Yin Wei; Min Shi
Journal:  Beilstein J Org Chem       Date:  2012-07-16       Impact factor: 2.883

6.  Expanding the chemical diversity of spirooxindoles via alkylative pyridine dearomatization.

Authors:  Chunhui Dai; Bo Liang; Corey R J Stephenson
Journal:  Beilstein J Org Chem       Date:  2012-07-02       Impact factor: 2.883

7.  Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition.

Authors:  Vipin Singh; Shanta Raj Lakshmi; L Raju Chowhan
Journal:  Front Chem       Date:  2022-01-11       Impact factor: 5.221

8.  Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines].

Authors:  Hui Zheng; Ying Han; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2022-06-14       Impact factor: 2.544

9.  Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione.

Authors:  Yan Sun; Jing Sun; Chao-Guo Yan
Journal:  Beilstein J Org Chem       Date:  2013-01-03       Impact factor: 2.883

Review 10.  Chiral phosphines in nucleophilic organocatalysis.

Authors:  Yumei Xiao; Zhanhu Sun; Hongchao Guo; Ohyun Kwon
Journal:  Beilstein J Org Chem       Date:  2014-09-04       Impact factor: 2.883

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