John Shugart - Use of cyclic allylic bromides in the zinc-mediated aqueous Barbier-Grignard reaction

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  Publication Details (including relevant citation   information):

  Breton,   Gary W.; Shugart, John H.; Hughey, C. A.; Conrad, B. P.; Perala,   S. M. Use of cyclic allylic bromides in the zinc-mediated   aqueous Barbier-Grignard reaction. Molecules (2001),   6(8), 655-662.


    The zinc–mediated aqueous Barbier–Grignard reaction of cyclic   allylic bromide substrates with various aldehydes and ketones to   afford homoallylic alcohols was investigated. Aromatic aldehydes   and ketones afforded adducts in good yields (66–90%) and with   good diastereoselectivities. Non–aromatic aldehydes also reacted   well under these conditions, but only poor yields were obtained   with non–aromatic ketones. Regioselectivity was high when some   substituted cyclic allylic bromides were investigated.

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