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

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

Gary W. Breton* email, John H. Shugart, Christine A. Hughey, Brian P. Conrad and Suzanne M. Perala
Department of Chemistry, Berry College, Mount Berry, GA 30149, USA
* 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.
Keywords: Barbier–Grignard reaction; aqueous reactions; organozinc; homoallylic alcohols

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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.

AMA Style

Breton GW, Shugart JH, Hughey CA, Conrad BP, Perala SM. Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction. Molecules. 2001; 6(8):655-662.

Chicago/Turabian Style

Breton, Gary W.; Shugart, John H.; Hughey, Christine A.; Conrad, Brian P.; Perala, Suzanne M. 2001. "Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction." Molecules 6, no. 8: 655-662.

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