Next Article in Journal
Stilbenes and a New Acetophenone Derivative from Scirpus holoschoenus
Previous Article in Journal
Synthesis, Structure and Antitumor Activity of Dibutyltin Oxide Complexes with 5-Fluorouracil Derivatives. Crystal Structure of [(5-Fluorouracil)-1-CH2CH2COOSn(n-Bu) 2]4O2
Molecules 2001, 6(8), 655-662; doi:10.3390/60800655
Article

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

* , , ,  and
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
Download PDF [35 KB, uploaded 18 June 2014]

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 Barbier–Grignard reaction; aqueous reactions; organozinc; homoallylic alcohols
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


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.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert