The University of Southampton
University of Southampton Institutional Repository

Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones

Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones
Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones
Alkyl and aryl Grignard reagents react with cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones by 1,il-addition to give as the major products, for example, cis-2,3-disubstituted tetrahydropyrans. In most examples ring opening leads to stereoselective formation of rearranged hemiketals as minor products. Under other conditions with 2,2,2-trifIuoro-1-(2-ethoxy-3,4-dihydro-2H-5-pyranyl)-1-ethanone stereoselective ring opening leads to acyclic aldehydes, as minor products and, by the major pathway, to a series of diols by addition of further equivalents of the Grignard reagent. Tn the absence of further Grignard reagent at higher temperatures internal hydride transfer can afford acyclic esters.
additions, a-strain, grignard reagents, hydride transfer, tetrahydropyrans, trifluoromethylketoneshuman-leukocyte elastase, benzyl copper reagents, ?-hydroxy ketones, tishchenko reactions, nonpeptidic inhibitors, antennal esterases, carbonyl-compounds, mediated addition, in-vitro, reduction
0040-4020
10039-10055
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
El-Tamany, E. S. H.
e500b10f-b3bd-4548-b0dd-bf05b4e83076
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe
El-Sagheer, A. H.
c37c0aa8-20a2-4fd9-b2cf-3a891182db00
El-Tamany, E. S. H.
e500b10f-b3bd-4548-b0dd-bf05b4e83076

Mellor, J. M., Reid, G., El-Sagheer, A. H. and El-Tamany, E. S. H. (2000) Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones. Tetrahedron, 56 (51), 10039-10055. (doi:10.1016/S0040-4020(00)00975-3).

Record type: Article

Abstract

Alkyl and aryl Grignard reagents react with cyclic ?-alkoxy-?, ?-unsaturated trifluoromethylketones by 1,il-addition to give as the major products, for example, cis-2,3-disubstituted tetrahydropyrans. In most examples ring opening leads to stereoselective formation of rearranged hemiketals as minor products. Under other conditions with 2,2,2-trifIuoro-1-(2-ethoxy-3,4-dihydro-2H-5-pyranyl)-1-ethanone stereoselective ring opening leads to acyclic aldehydes, as minor products and, by the major pathway, to a series of diols by addition of further equivalents of the Grignard reagent. Tn the absence of further Grignard reagent at higher temperatures internal hydride transfer can afford acyclic esters.

This record has no associated files available for download.

More information

Published date: 15 December 2000
Keywords: additions, a-strain, grignard reagents, hydride transfer, tetrahydropyrans, trifluoromethylketoneshuman-leukocyte elastase, benzyl copper reagents, ?-hydroxy ketones, tishchenko reactions, nonpeptidic inhibitors, antennal esterases, carbonyl-compounds, mediated addition, in-vitro, reduction

Identifiers

Local EPrints ID: 18929
URI: http://eprints.soton.ac.uk/id/eprint/18929
ISSN: 0040-4020
PURE UUID: 8d368514-bb2c-4746-9adc-9a8b58ed4873

Catalogue record

Date deposited: 16 Dec 2005
Last modified: 15 Mar 2024 06:09

Export record

Altmetrics

Contributors

Author: J. M. Mellor
Author: G. Reid
Author: A. H. El-Sagheer
Author: E. S. H. El-Tamany

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

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×