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Catalytic Asymmetric Mannich/Cyclization of 2-Isothiocyanato-1-indanones: An Approach to the Synthesis of Bispirocyclic Indanone-Thioimidazolidine-Oxindoles. | LitMetric

AI Article Synopsis

  • The study highlights how new isothiocyanates from 1-indanones can effectively participate in heteroannulation reactions with isatinimines, showcasing their role as valuable building blocks.
  • This is achieved through a convenient Mannich/cyclization cascade reaction, which enables the efficient creation of complex bispirocyclic indanone-thioimidazolidine-oxindoles with remarkable yields and selectivity.
  • Additionally, the research demonstrates that these products can be transformed into various other potentially bioactive bispirocyclic heterocycles, expanding their applicability in pharmaceutical development.

Article Abstract

This study demonstrates that novel isothiocyanates derived from 1-indanones are useful building blocks in heteroannulation reactions with isatinimines. This convenient Mannich/cyclization cascade reaction serves as a powerful tool for the enantioselective construction of bispirocyclic indanone-thioimidazolidine-oxindoles bearing two adjacent spiro-quaternary stereocenters in good to excellent yields with excellent diastereo- and enantioselectivities. Versatile transformations of the products into other potential bioactive bispirocyclic heterocycles have also been demonstrated.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b01389DOI Listing

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