A domino [3+2] cycloaddition/deamination/imine hydrolysis reaction of cyclopropyl spirooxindoles with thiourea for access to spiro-γ-thiolactone oxindoles

• Published in: ORGANIC CHEMISTRY FRONTIERS Vol. 11; no. 16; pp. 4416 - 4422
• Main Authors: Wang, Hai-Ting, Wen, Xiao-Lin, Xu, Xiao-Lin, Wang, Dong-Chao, Guo, Hai-Ming
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 06.08.2024; Royal Society of Chemistry
• Subjects: Biological activity; Chemistry; Chemistry, Organic; Cycloaddition; Cyclopropane; Deamination; Hydrolysis; Intermediates; Organic compounds; Physical Sciences; Science & Technology; Thiolactone; Thiourea; Thioureas; DONOR-ACCEPTOR CYCLOPROPANES; MOLECULAR HYBRIDIZATION; POTENT; DESIGN; THIOL; CYCLOADDITIONS; ALDEHYDES; INHIBITORS; DERIVATIVES
• ISSN: 2052-4129; 2052-4110; 2052-4110
• DOI: 10.1039/d4qo00833b

A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of D-A cyclopropane with inexpensive thiourea catalyzed by Lu(OTf)3 has been developed. A series of gamma-thiolactone spirooxindole compounds with potential biological activity were obtained in up to 98% yields. Experiments to investigate the mechanism showed that gamma-thiolactone products were from the hydrolysis of the imine intermediates. In addition, the asymmetric catalytic reaction of D-A cyclopropane and thiourea has been successfully developed to afford spiro-gamma-thiolactone compounds with good enantioselectivities (up to 98% ee). The utility of this method was showcased by the facile transformation and biological activity of products. A Lu(OTf)3-catalyzed domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of D-A cyclopropane with thiourea was developed to afford gamma-thiolactone spirooxindoles.