LrgpV1, Main, Exploration, bibRecord, 001868

Strict base dependence of chirality transfer on [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether

Identifieur interne : 001868 ( Main/Exploration ); précédent : 001867; suivant : 001869

Strict base dependence of chirality transfer on [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether

Auteurs : Toshiyuki Itoh [Japon] ; Kazutoshi Kudo [Japon]

Source :

Tetrahedron Letters [ 0040-4039 ] ; 2001.

RBID : ISTEX:1B859571BAA31E1A45991881D68AEA103742953E

English descriptors

KwdEn :
- Allyl, Allyl ether, Allylic, Allylic ether, Chem, Equiv, Et2o, Ether, Itoh, Kudo, Kudo tetrahedron letters, Lett, Ltmp, Optical purity, Pathway, Quenched, Radical pathway mechanism, Reaction mechanism, Rearrangement, Rearrangement product, Stereochemistry, Stereoselectivity, Tetrahedron, Tetrahedron lett, Uorine, [2,3]-Wittig rearrangement, optically active 1,1,2-trifluoroallylic ether, radical pathway.
Teeft :
- Allyl, Allyl ether, Allylic, Allylic ether, Chem, Equiv, Et2o, Ether, Itoh, Kudo, Kudo tetrahedron letters, Lett, Ltmp, Optical purity, Pathway, Quenched, Radical pathway mechanism, Reaction mechanism, Rearrangement, Rearrangement product, Stereochemistry, Stereoselectivity, Tetrahedron, Tetrahedron lett, Uorine.

Abstract

Abstract: Investigation of [2,3]-Wittig rearrangement of optically active 1,1,2-trifluoroallylic ether revealed that chirality transfer of the starting compound strictly depended on the base employed, while stereoselectivity of the newly formed olefinic part was controlled with perfect (E)-selectivity. Because the reaction was inhibited by addition of TEMPO; these results suggested [2,3]-Wittig reaction proceeded via a radical pathway mechanism.

Url:

https://api.istex.fr/document/1B859571BAA31E1A45991881D68AEA103742953E/fulltext/pdf

DOI: 10.1016/S0040-4039(00)02236-X

Affiliations:

Japon

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Le document en format XML

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<term>Tetrahedron</term>
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<front><div type="abstract" xml:lang="en">Abstract: Investigation of [2,3]-Wittig rearrangement of optically active 1,1,2-trifluoroallylic ether revealed that chirality transfer of the starting compound strictly depended on the base employed, while stereoselectivity of the newly formed olefinic part was controlled with perfect (E)-selectivity. Because the reaction was inhibited by addition of TEMPO; these results suggested [2,3]-Wittig reaction proceeded via a radical pathway mechanism.</div>
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Strict base dependence of chirality transfer on [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether

Strict base dependence of chirality transfer on [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether

Source :

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri