Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-?, ?-unsaturated trifluoromethylketones
Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-?, ?-unsaturated trifluoromethylketones
Benzyl Grignard reagents react with cyclic ?-alkoxy-?, ? -unsaturated trifluoromethyl ketones by 1,2-addition to afford unsaturated allylic alcohols in high yield. The factors determining the balance between 1,2- and 1,4-addition to unsaturated ketones are discussed. The structures of major and minor products are established by single crystal X-ray diffraction studies.
additions, grignard reagents, trifluoromethylketones
?, ?-unsaturated carbonyl-compounds, ?-enones, ?, ?-ethylenic ketones, regioselectivity, chloride, stereochemistry
10057-10066
Coles, S. J.
503a9d9c-0380-4fcd-ad31-cd329255c08e
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
Salem Eedm Metwally, R. N.
b47db6e4-bc62-473c-94ed-c8464adabd34
15 December 2000
Coles, S. J.
503a9d9c-0380-4fcd-ad31-cd329255c08e
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
Salem Eedm Metwally, R. N.
b47db6e4-bc62-473c-94ed-c8464adabd34
Coles, S. J., Mellor, J. M., El-Sagheer, A. H. and Salem Eedm Metwally, R. N.
(2000)
Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic beta-alkoxy-?, ?-unsaturated trifluoromethylketones.
Tetrahedron, 56 (51), .
(doi:10.1016/S0040-4020(00)00976-5).
Abstract
Benzyl Grignard reagents react with cyclic ?-alkoxy-?, ? -unsaturated trifluoromethyl ketones by 1,2-addition to afford unsaturated allylic alcohols in high yield. The factors determining the balance between 1,2- and 1,4-addition to unsaturated ketones are discussed. The structures of major and minor products are established by single crystal X-ray diffraction studies.
This record has no associated files available for download.
More information
Published date: 15 December 2000
Keywords:
additions, grignard reagents, trifluoromethylketones
?, ?-unsaturated carbonyl-compounds, ?-enones, ?, ?-ethylenic ketones, regioselectivity, chloride, stereochemistry
Identifiers
Local EPrints ID: 18928
URI: http://eprints.soton.ac.uk/id/eprint/18928
ISSN: 0040-4020
PURE UUID: f8901d9e-7294-4f9e-a1e4-a8ad08ddc629
Catalogue record
Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:09
Export record
Altmetrics
Contributors
Author:
S. J. Coles
Author:
J. M. Mellor
Author:
A. H. El-Sagheer
Author:
R. N. Salem Eedm Metwally
Download statistics
Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.
View more statistics