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Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate (1994)

Inoue, Hirohumi ; Murata, Shizuaki ; Suzuki, Toshiyasu

Weinheim : Wiley-Blackwell

Liebigs Annalen 1994 (1994), S. 901-909

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ISSN: 0170-2041

Schlagwort(e): Oxyselenenylation ; Benzeneselenenyl triflate ; Selenium compounds ; Trifluoromethanesulfonate ; Alkenols ; Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Oxyselenylation of 4-substituted 5-hexen-1-ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3-substituted trans- or cis-2-(phenylselenenylmethyl)tetrahydropyrans 3. Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4-position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl. The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8.

Zusätzliches Material: 2 Tab.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/jlac.199419940910

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