Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 22, Pages 6885-6894Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200358
Keywords
cycloaddition; asymmetric synthesis; multicomponent reactions; organocatalysis; spiro compounds
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Funding
- MOST [2009CB82530]
- Ministry of Education
- NSFC [20732006, 21002083, 21072181]
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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.
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