A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates |
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Authors: | Fandrick Keith R Fandrick Daniel R Reeves Jonathan T Gao Joe Ma Shengli Li Wenjie Lee Heewon Grinberg Nelu Lu Bruce Senanayake Chris H |
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Institution: | Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. keith.fandrick@boehringer-ingelheim.com |
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Abstract: | An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which γ-butyrolactones, β-hydroxy methyl ketones, and β-hydroxycarboxylates are readily obtained. |
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