Reaction of alkyl and aryl grignard reagents with trifluoroacetyldihydropyrans and other cyclic β-alkoxy-α, β-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 β-alkoxy-α, β-unsaturated trifluoromethylketones. Tetrahedron, 56, (51), 10039-10055. (doi:10.1016/S0040-4020(00)00975-3).

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Description/Abstract

Alkyl and aryl Grignard reagents react with cyclic β-alkoxy-α, β-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.

Item Type: Article
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Keywords: additions, a-strain, grignard reagents, hydride transfer, tetrahydropyrans, trifluoromethylketoneshuman-leukocyte elastase, benzyl copper reagents, β-hydroxy ketones, tishchenko reactions, nonpeptidic inhibitors, antennal esterases, carbonyl-compounds, mediated addition, in-vitro, reduction
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 18929
Date Deposited: 16 Dec 2005
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/18929

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