Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification

Carmela Aprile, Michelangelo Gruttadauria, Paolo Lo Meo, Serena Riela, Renato Noto

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

Eight unsaturated alcohols were cyclized by selenoetherification in 6-exo or 6-endo manner to give substituted tetrahydropyran rings. Yields, regio- and stereoselectivities were discussed in terms of steric and electronic effects such as Se-O interaction. For the first time examples of the use of silica gel in selenoetherification and the effect of the X- counter ion of PhSe+ on the reaction course are discussed. These effects are related to the occurrence of Se-O interaction.

langue originaleAnglais
Pages (de - à)293-305
Nombre de pages13
journalHeterocycles
Volume57
Numéro de publication2
étatPublié - 1 févr. 2002

Empreinte digitale

Stereoselectivity
Regioselectivity
Radiation counters
Silica Gel
Alcohols
Ions

Citer ceci

Aprile, Carmela ; Gruttadauria, Michelangelo ; Lo Meo, Paolo ; Riela, Serena ; Noto, Renato. / Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification. Dans: Heterocycles. 2002 ; Vol 57, Numéro 2. p. 293-305.
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Aprile, C, Gruttadauria, M, Lo Meo, P, Riela, S & Noto, R 2002, 'Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification', Heterocycles, VOL. 57, Numéro 2, p. 293-305.

Stereoselective synthesis of substituted tetrahydropyran rings via 6-exo and 6-endo selenoetherification. / Aprile, Carmela; Gruttadauria, Michelangelo; Lo Meo, Paolo; Riela, Serena; Noto, Renato.

Dans: Heterocycles, Vol 57, Numéro 2, 01.02.2002, p. 293-305.

Résultats de recherche: Contribution à un journal/une revueArticle

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