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ORGANIC LETTERS
Volume -, Issue -, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02170
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- EPSRC [EP/S019359/1, EP/T023643/1]
- Syngenta
- EPSRC Centre for Doctoral Training in Critical Resource Catalysis [CRITICAT] [EP/L016419/1]
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This study reports a method for enantioselective [2 + 2] cycloaddition of C(1) ammonium enolates generated catalytically using the isothiourea HyperBTM with N-alkyl isatins, which leads to the formation of spirocyclic beta-lactones. In situ ring opening with an amine nucleophile generates isolable highly enantioenriched products with a diastereomeric ratio of up to 92:8 and an enantiomeric ratio of > 99:1.
Enantioselective [2 + 2] cycloaddition of C(1) ammonium enolates generated catalytically using the isothiourea HyperBTM with N-alkyl isatins gives spirocyclic beta-lactones. In situ ring opening with an amine nucleophile generates isolable highly enantioenriched products in up to 92:8 dr and in > 99:1 er.
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