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

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 alde...

Descripción completa

Detalles Bibliográficos
Autores principales: Breton, Gary W., Shugart, John H., Hughey, Christine A., Conrad, Brian P., Perala, Suzanne M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2001
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236354/
http://dx.doi.org/10.3390/60800655
_version_ 1783371018757210112
author Breton, Gary W.
Shugart, John H.
Hughey, Christine A.
Conrad, Brian P.
Perala, Suzanne M.
author_facet Breton, Gary W.
Shugart, John H.
Hughey, Christine A.
Conrad, Brian P.
Perala, Suzanne M.
author_sort Breton, Gary W.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6236354
institution National Center for Biotechnology Information
language English
publishDate 2001
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62363542018-11-19 Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction Breton, Gary W. Shugart, John H. Hughey, Christine A. Conrad, Brian P. Perala, Suzanne M. Molecules Article 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. MDPI 2001-07-31 /pmc/articles/PMC6236354/ http://dx.doi.org/10.3390/60800655 Text en © 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Breton, Gary W.
Shugart, John H.
Hughey, Christine A.
Conrad, Brian P.
Perala, Suzanne M.
Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title_full Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title_fullStr Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title_full_unstemmed Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title_short Use of Cyclic Allylic Bromides in the Zinc–Mediated Aqueous Barbier–Grignard Reaction
title_sort use of cyclic allylic bromides in the zinc–mediated aqueous barbier–grignard reaction
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236354/
http://dx.doi.org/10.3390/60800655
work_keys_str_mv AT bretongaryw useofcyclicallylicbromidesinthezincmediatedaqueousbarbiergrignardreaction
AT shugartjohnh useofcyclicallylicbromidesinthezincmediatedaqueousbarbiergrignardreaction
AT hugheychristinea useofcyclicallylicbromidesinthezincmediatedaqueousbarbiergrignardreaction
AT conradbrianp useofcyclicallylicbromidesinthezincmediatedaqueousbarbiergrignardreaction
AT peralasuzannem useofcyclicallylicbromidesinthezincmediatedaqueousbarbiergrignardreaction

Ejemplares similares