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

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–thioi...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 13; pp. 3797 - 3800
Main Authors Zhao, Bo-Liang, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2018
Amer Chemical Soc
Subjects
chemical structure
Chemistry
Chemistry, Organic
cyclization reactions
enantioselectivity
isothiocyanates
Physical Sciences
Science & Technology
ISOTHIOCYANATO OXINDOLES
DOMINO REACTIONS
ENANTIOSELECTIVE SYNTHESIS
3-ISOTHIOCYANATO OXINDOLES
CONSTRUCTION
BETA-KETO-ESTERS
MICHAEL ADDITION/CYCLIZATION
POLYCYCLIC SPIROOXINDOLES
HIGHLY EFFICIENT
CASCADE REACTION
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.8b01389