Abstract
A novel organocatalytic asymmetric [3 + 2] cycloaddition reaction between methyleneindolinones and allylic compounds yielding complex spirocyclopentaneoxindoles has been developed. It provides extraordinary levels of enantioselective control involving a chiral phosphine as a nucleophilic organocatalyst. Simple precursors were used under mild conditions to construct oxindole derivatives with high enantiopurity and structural diversity. This method should be useful in medicinal chemistry and diversity-oriented syntheses of these intriguing compounds.
Original language | English |
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Pages (from-to) | 4672-4675 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 133 |
Issue number | 13 |
DOIs | |
Publication status | Published - 6 Apr 2011 |
Publication type | A1 Journal article-refereed |
Funding
Research support from the Skaggs Institute for Chemical Biology is gratefully acknowledged. N.R.C. thanks Fundacao para a Ciencia e Tecnologia (SFRH/BPD/46589/2008) for financial support. We also thank Dr. A. L. Rheingold for the X-ray crystallographic analysis.
Keywords
- ASYMMETRIC ASSEMBLY REACTIONS
- MODIFIED ALLYLIC COMPOUNDS
- PHOSPHORUS YLIDE REACTION
- MICHAEL-HENRY REACTIONS
- BAYLIS-HILLMAN REACTION
- DIELS-ALDER REACTIONS
- ANNULATION REACTION
- DOMINO REACTIONS
- 4 STEREOCENTERS
- MULTISUBSTITUTED CYCLOPENTANES