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Volumn 7, Issue 6, 2005, Pages 1113-1116

Stereoselective synthesis of tetrahydropyran-4-ones from dioxinones catalyzed by scandium(III) triflate

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHEMICAL COMPOUND; DIOXIN; ENOL ETHER; ETHER DERIVATIVE; OXIDE; SCANDIUM; SCANDIUM TRIFLATE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 18244407272     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050093v     Document Type: Article
Times cited : (51)

References (39)
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    • The appended carboxy substituent significantly attenuates the reactivity of dienes related to 1, thereby rendering a hetero-Diels-Alder strategy to compounds such as 4 currently untenable under numerous Lewis acid catalyzed conditions surveyed.
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    • Lower catalysts loadings (5 and 10 mol %) increase reaction time but do not adversely affect yield or selectivity
    • Lower catalysts loadings (5 and 10 mol %) increase reaction time but do not adversely affect yield or selectivity.
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    • An alternative mechanism may involve an oxonia-Cope rearrangement of I followed by ring closure; see: (a) Semeyn, C.; Blaauw, R. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1997, 62, 3426-3427. (b) Rychnovsky, S. D.; Marumoto, S.; Jaber, J. J. Org. Lett. 2001, 3, 3815-3818 and references therein. (c) Roush, W. R.; Dilley, G. J. Synlett 2001, 955-959. Further investigations to probe the operative reaction pathway are ongoing in our laboratory.
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    • 1H coupling values (J ≥ 10 Hz) indicating a diaxial vicinal proton disposition
    • 1H coupling values (J ≥ 10 Hz) indicating a diaxial vicinal proton disposition.
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