Synlett

Direct Conversion of Aldehydes and Ketones to Allylic Halides by a NbX5-[3, 3] Rearrangement

FF Fleming, PC Ravikumar, L Yao

Index: Fleming, Fraser F.; Ravikumar; Yao, Lihua Synlett, 2009 , # 7 p. 1077 - 1080

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Citation Number: 8

Abstract

Abstract Sequential addition of vinylmagnesium bromide and NbCl 5, or NbBr 5, to a series of aldehydes and ketones directly provides homologated, allylic halides. Transposition of the intermediate vinyl alkoxide is envisaged through a metalo-halo-[3, 3] rearrangement with concomitant delivery of the halogen to the terminal carbon. The [3, 3] rearrangement is equally effective for the conversion of a propargyllic alcohol to the corresponding allenyl ...

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