New spirocyclic oxindole synthesis based on a hetero Claisen rearrangement |
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Authors: | Mao Zhan Baldwin Steven W |
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Institution: | Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA. |
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Abstract: | reaction: see text] A new method for preparing spirocyclic oxindoles is presented. Featuring a 3,3]-sigmatropic enolate rearrangement, the three-step process converts carboxylic acid starting materials to oxidnole products in overall yields of 52-76%. The enolate rearrangement step occurs at -78 degrees C and provides easy access to oxindole products that have previously been difficult to prepare. |
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