Literature DB >> 24346948

One-pot tandem approach to spirocyclic oxindoles featuring adjacent spiro-stereocenters.

Yun-Lin Liu1, Xin Wang, Yu-Lei Zhao, Feng Zhu, Xing-Ping Zeng, Long Chen, Cui-Hong Wang, Xiao-Li Zhao, Jian Zhou.   

Abstract

All in a sequence: An organocatalyzed Morita-Baylis-Hillman (MBH)/bromination/[3+2] annulation sequence for highly stereoselective syntheses of bis(spirooxindole)s featuring adjacent spiro-stereocenters is described. The key step is an unprecedented catalytic asymmetric [3+2] annulation of isatin-derived MBH adducts, containing a tetrasubstituted alkene moiety, with isatins.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; heterocycles; organocatalysis; spiro compounds; synthetic methods

Mesh:

Substances:

Year:  2013        PMID: 24346948     DOI: 10.1002/anie.201307250

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  3 in total

1.  A convenient approach to difluoromethylated all-carbon quaternary centers via Ni(ii)-catalyzed enantioselective Michael addition.

Authors:  Xuan Yu; Hui Bai; Dong Wang; Zhaohai Qin; Jia-Qi Li; Bin Fu
Journal:  RSC Adv       Date:  2018-05-25       Impact factor: 3.361

2.  Tosylhydrazine-promoted self-conjugate reduction-Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives.

Authors:  Sayan Pramanik; Chhanda Mukhopadhyay
Journal:  Beilstein J Org Chem       Date:  2022-04-27       Impact factor: 2.544

3.  Highly Efficient and Stereoselective Construction of Bispirooxindole Derivatives via a Three-Component 1,3-Dipolar Cycloaddition Reaction.

Authors:  Qin Xu; De Wang; Yin Wei; Min Shi
Journal:  ChemistryOpen       Date:  2014-06-18       Impact factor: 2.911

  3 in total

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