Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones

Graalfs H, Fröhlich R, Wolff C, Mattay J (1999)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (5): 1057-1073.

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Abstract
Intermolecular addition of radicals to the 1,3-dioxin-4-ones la,b and 2a,b with (-)-menthone incorporated as chiral auxiliary in 2-position were investigated. Photochemically generated radicals from I,3-dioxolane, oxolane, and 2-propanol were added with high facial selectivity from the more exposed a-side. Intramolecular addition of 1,3-dioxolan-2-yl radicals to chiral dioxinones proceeded less efficiently and with lower selectivity also from the a-side. Nevertheless, it was possible to form the new spirocyclic compounds 22-27. The 1,3-dioxin-4-ones 32a,b possessing an unsaturated side chain were attacked by radicals at the terminal double bond. In the case of irradiation of 32b in 1,3-dioxolane a cyclization followed the intermolecular addition of a 1,3-dioxolan-2-yl radical and the dispiro compound 36 was formed. However, the formation of dispiro compound 40 required two reaction steps starting with irradiation of 32b and bromotrichloromethane. The achiral 1,3-dioxin-4-one 44 possessing an unsaturated side chain at C-2 was attacked by 1,3-dioxolan-2-yl radicals preferentially at C-6.
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Graalfs H, Fröhlich R, Wolff C, Mattay J. Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1999;(5):1057-1073.
Graalfs, H., Fröhlich, R., Wolff, C., & Mattay, J. (1999). Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(5), 1057-1073.
Graalfs, H., Fröhlich, R., Wolff, C., and Mattay, J. (1999). Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1057-1073.
Graalfs, H., et al., 1999. Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (5), p 1057-1073.
H. Graalfs, et al., “Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, pp. 1057-1073.
Graalfs, H., Fröhlich, R., Wolff, C., Mattay, J.: Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1057-1073 (1999).
Graalfs, H, Fröhlich, R, Wolff, C, and Mattay, Jochen. “Diastereoselective addition of radicals to chiral 1,3-dioxin-4-ones”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 5 (1999): 1057-1073.
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