Alkylation of magnesium enamide with alkyl chlorides and fluorides

Alkylation of magnesium enamide with alkyl chlorides and fluorides
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DOI:
10.1021/ja055306q
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发表时间:
2005-10-19
影响因子:
15
通讯作者:
Nakamura, B
Nakamura, B
中科院分区:
化学1区
文献类型:
--
作者:
Hatakeyama, T;Ito, S;Nakamura, B

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由N-2-(N ′,N ′-二乙基氨基)乙基亚胺衍生的烯酰胺镁与伯烷基氯和仲烷基氯或伯烷基氟反应,水解后以良好至优异的产率得到α-烷基化酮。该反应在亲电碳中心发生高水平的立体化学反转,并将用于制备光学活性化合物。
A magnesium enamide derived fromN-2-(N‘,N‘-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.