Asymmetric Mannich/Cyclization Reaction of 2-Benzothiazolimines and 2-Isothiocyano-1-indanones to Construct Chiral Spirocyclic Compounds

An efficient and practical organocatalyzed asymmetric Mannich/cyclization tandem reaction strategy of 2-benzothiazolimines and 2-isothiocyanato-1-indanones was developed, and novel spirocyclic compounds containing benzothiazolimine and indanone scaffolds were obtained. This chiral thiourea-catalyzed...

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Published inMolecules (Basel, Switzerland) Vol. 29; no. 13; p. 2958
Main Authors Zheng, Yao, Du, Da-Ming
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 21.06.2024
Subjects
2-isothiocyanato-1-indanone
benzothiazole
Hydrocarbons
imine
Mannich reaction
2-isothiocyanato-1-indanone
Mannich reaction
benzothiazole
imine
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Summary:An efficient and practical organocatalyzed asymmetric Mannich/cyclization tandem reaction strategy of 2-benzothiazolimines and 2-isothiocyanato-1-indanones was developed, and novel spirocyclic compounds containing benzothiazolimine and indanone scaffolds were obtained. This chiral thiourea-catalyzed Mannich/cyclization tandem reaction offers chiral spirocyclic compounds with continuous tertiary and quaternary stereocenters in good to high yields (up to 90%) with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 98% ee) at −18 °C. Additionally, the scaled-up synthesis was also performed with retained yield and stereoselectivity, and a reaction mechanism was also proposed.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29132958