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Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita-Baylis-Hillman Reaction.
- Source :
-
Journal of the American Chemical Society . 11/3/2010, Vol. 132 Issue 43, p15176-15178. 3p. 1 Chart. - Publication Year :
- 2010
-
Abstract
- We report a highly enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins and acrolein to provide enantiomerically enriched 3-substituted 3-hydroxyoxindoles, which could serve as valuable synthetic building blocks. This is also the first time that a ketone has been used as the electrophile and acrolein as the nucleophile in a highly enantioselective catalytic asymmetric MBH reaction. Hatakeyama's catalyst, β-isocupreidine (1), turned out to be a powerful catalyst for this transformation. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00027863
- Volume :
- 132
- Issue :
- 43
- Database :
- Academic Search Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 55093132
- Full Text :
- https://doi.org/10.1021/ja107858z