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Molecules 2001, 6(8), 655-662; doi:10.3390/60800655

Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction

Department of Chemistry, Berry College, Mount Berry, GA 30149, USA
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Author to whom correspondence should be addressed.
Received: 27 February 2001 / Accepted: 12 June 2001 / Published: 31 July 2001
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Abstract

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. View Full-Text
Keywords: Barbier–Grignard reaction; aqueous reactions; organozinc; homoallylic alcohols Barbier–Grignard reaction; aqueous reactions; organozinc; homoallylic alcohols
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Breton, G.W.; Shugart, J.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, 655-662.

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