Palladium-catalyzed reaction of nucleophiles with diacetates of allylic 1,1-diols |
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| Authors: | Xiyan Lu Yujin Huang |
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| Institution: | Shanghai Institute of Organic Chemistry, Academia Sinica, 345 Lingling Lu, Shanghai 200032 China |
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| Abstract: | The reactions of allylic 1,1-diol diacetates (I) with carbanions under the catalysis of Pd(PPh3)4 were studied. Sodium diethyl malonate reacted with I to form an abnormal product resulting from the attack of the diethyl malonate carbanion on the carbonyl carbon of the acetoxy group, while sodium diethyl acetylmalonate gave the normal reaction products with high regioselectivity. The mechanisms of these reactions are discussed. |
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