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Synlett 2001; 2001(12): 1847-1850
DOI: 10.1055/s-2001-18751
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Substrate-Induced Diastereoselectivity in the Dimethyldioxirane Epoxidation of Simple Alkenes and Dienes

Amalia Asouti* , Lazaros P. Hadjiarapoglou
  • *Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece; Fax: + 30(651)98799; E-mail: LXATZIAR@cc.uoi.gr
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Publication Date:
04 December 2001 (online)

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Various alkenes and dienes, such as (R)- or (S)-limonene 2, 2-carene 6, 3-carene 8, (R)-α-pinene 10, (S)-α-pinene 12, and endo-dicyclopentadiene 14 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). The selectivity observed in these epoxidations is explained by the assumption of hydrogen bonding between bridge protons and the dioxirane.

dimethyldioxirane - epoxidation - diasteroselectivity - regioselectivity

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