Journal
ORGANIC LETTERS
Volume 13, Issue 1, Pages 82-85Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol102597s
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- National University of Singapore
- Ministry of Education (MOE) of Singapore [R-143-000-362-112]
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The first tertiary amine catalyzed enantioselective Morita-Baylis-Hillman (MBH) reaction of isatins with acrylates has been demonstrated, allowing asymmetric synthesis of biologically significant 3-substituted-3-hydroxy-2-oxindoles in good yields and with excellent enantioselectivities. The C6'-OH group of beta-isocupreidine (beta-ICD) is believed to facilitate the key proton transfer step in the MBH reaction, via an intramolecular proton relay process.
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