Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 10, Pages 1935-1944Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101810
Keywords
Organocatalysis; Heterocycles; Michael addition; Reduction; Spiroox-ind-oles
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Funding
- National Natural Science Foundation of China [20772113, 21072145]
- Foundation for the Author of National Excellent Doctoral Dissertation of PR China [200931]
- Natural Science Foundation of Jiangsu Province of China [BK2009115]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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Heterocyclic spirooxindoles that bear a multisubstitutedheterocyclic motif and quaternary stereocenter at the 3-position are prevalent in a large number of spirooxindole alkaloids, which are pharmaceutically relevant compounds with remarkable biological activities. In this paper, we report an efficient method for the construction of enantiomerically enriched spiro[2H-pyran-3,4'-indoline] derivatives by a systematic Michael/reduction/cyclization sequence. The initial Michael addition of isatylidenemalononitriles with ketones was catalyzed by a cinchona-based chiral primary amine and L-camphorsulfonic acid and furnished multifunctional, optically active Michael adducts in high yields (8199?%) with excellent enantioselectivities (95 to >99?% ee). Subsequently, the Michael adducts were converted into spiro[2H-pyran-3,4'-indoline] derivatives in 5293?% yields with 1.5:1 to 20:1 diastereomeric ratio and 9099?% ee by utilizing NaBH4 as a cascade reduction/cyclization reagent.
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