Functionalized organozincates and organocuprates derived from γ-hydroxytellurides in the preparation of 1,4-hydroxyketones

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• 作者：Jefferson L. Princival ; Alcindo A. Dos Santos ; Joã ; o V. Comasseto
• 关键词：Hydroxyltellurides ; Organozincates ; Organocuprates ; 1 ; 4-Hydroxyketones
• 刊名：Tetrahedron Letters
• 出版年：2009
• 出版时间：18 November 2009
• 年：2009
• 卷：50
• 期：46
• 页码：6368-6371
• 全文大小：1761 K

文摘

A C–O-dianionic zincate was generated by a Te/Li exchange reaction of an alkyltelluride, followed by Li/Zn transmetallation and reaction with methyllithium. The reaction between the enantiomerically pure (99 % ee) (R)-dianionic zincate and benzoyl chloride led to 3-hydroxy-1-phenyl pentanone with total retention of the carbon configuration (99 % ee). Similar results were obtained using the corresponding Lipshutz cyanocuprates.