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

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Article

Princival, Jefferson L.¹  Dos Santos, Alcindo A.¹  Comasseto, Joao V.¹ 

[1] Univ Sao Paulo, Inst Quim, BR-05508900 Sao Paulo, Brazil

关键词: Hydroxyltellurides;    Organozincates;    Organocuprates;    1,4-Hydroxyketones;   

DOI  :  10.1016/j.tetlet.2009.08.097

来源: Elsevier

【 摘 要 】

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. (C) 2009 Elsevier Ltd. All rights reserved.

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