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

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), pp. 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.

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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: 17 Jul 2017 16:34

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Contributors

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

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