Studies on t-BuOK-catalyzed Michael addition of 1,2-allenic ketones with 2-substituted diethyl malonates: highly selective synthesis of β,γ-unsaturated enones |
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| Authors: | Shengming Ma Shichao Yu |
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| Institution: | a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China
b Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China |
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| Abstract: | In this paper, we have demonstrated a facile nucleophilic addition of 2-substituted diethyl malonate to various substituted 1,2-allenic ketones to afford β,γ-unsaturated enones using a catalytic amount of t-BuOK as the base. The reaction usually completes within 10 min in acetone at room temperature. The stereoselectivity of the reaction with γ-substituted allenic ketones is very high affording the β,γ-unsaturated E-enones. |
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| Keywords: | Michael addition 1 2-Allenic ketones β γ-Unsaturated enone Catalysis |
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