Design, Synthesis, and Resolution of Spirocyclic Bisoxindole-Based C 2 -Symmetric Diols

A new type of spirocyclic bisoxindole-based C -symmetric diols (SBIDOLs) was designed and synthesized. A series of racemic SBIDOL derivatives ( ) were readily synthesized from commercially available 2-halo-5-methoxyanilines (X = Cl or Br) through N-mono alkylation, acylation, oxidation, double intra...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-08, Vol.85 (16), p.10584-10592
Main Authors: Sun, Guodong, Wang, Zhongqing, Luo, Zhonghua, Lin, Yicao, Deng, Zhuofei, Li, Ridong, Zhang, Jiancun
Format: Article
Language:English
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Summary:A new type of spirocyclic bisoxindole-based C -symmetric diols (SBIDOLs) was designed and synthesized. A series of racemic SBIDOL derivatives ( ) were readily synthesized from commercially available 2-halo-5-methoxyanilines (X = Cl or Br) through N-mono alkylation, acylation, oxidation, double intramolecular Friedel-Crafts reaction, and demethylation reactions. The optical resolution of racemic was achieved via fractional crystallization of their bis-l-menthoxycarboxylates. Further modifications of SBIDOLs were investigated, leading to 5,5'-diaryl SBIDOL derivatives ( and ) through Pd-catalyzed Suzuki coupling and DM-SBIDOL by Pd/C-catalyzed hydrogenative dechlorination reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01155