TY - JOUR T1 - Scaffold-inspired enantioselective synthesis of biologically important spiro[pyrrolidin-3,2'-oxindoles] with structural diversity through catalytic isatin-derived 1,3-dipolar cycloadditions. AU - Shi,Feng, AU - Tao,Zhong-Lin, AU - Luo,Shi-Wei, AU - Tu,Shu-Jiang, AU - Gong,Liu-Zhu, Y1 - 2012/04/13/ PY - 2012/02/02/received PY - 2012/4/17/entrez PY - 2012/4/17/pubmed PY - 2012/10/30/medline SP - 6885 EP - 94 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 22 N2 - Catalytic asymmetric construction of the biologically important spiro[pyrrolidin-3,2'-oxindole] scaffold with contiguous quaternary stereogenic centers in excellent stereoselectivities (up to >99:1 d.r., 98% ee) has been established by using an organocatalytic 1,3-dipolar cycloaddition of isatin-based azomethine ylides. This protocol represents the first example of catalytic asymmetric 1,3-dipolar cycloadditions involving azomethine ylides generated in situ from unsymmetrical cyclic ketones. In addition, theoretical calculations were performed on the transition state of the reaction to understand the stereochemistry. Preliminary bioassays with these spiro[pyrrolidin-3,2'-oxindole] revealed that several compounds showed moderate cytotoxicity to SW116 cells. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22505189/Scaffold_inspired_enantioselective_synthesis_of_biologically_important_spiro[pyrrolidin_32'_oxindoles]_with_structural_diversity_through_catalytic_isatin_derived_13_dipolar_cycloadditions_ L2 - https://doi.org/10.1002/chem.201200358 DB - PRIME DP - Unbound Medicine ER -