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Epoxidation of allylic hydroperoxides by dimethyldioxirane and peroxy acids
Author(s) -
AbouElzahab Mohamed,
Adam Waldemar,
SahaMöller Chantu R.
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910181
Subject(s) - dimethyldioxirane , allylic rearrangement , chemistry , diastereomer , epoxy , organic chemistry , catalysis
The epoxidation of allylic hydroperoxides 2a–h by dimethyldioxirane afforded the epoxy hydroperoxides 3a–h in very good yields. On the other hand, only the substrates 2a, b and 2d–f can be converted into the corresponding epoxy hydroperoxides by peroxy acids in reasonable to good yields. The peroxy acid and dimethyldioxirane epoxidations of allylic hydroperoxides proceed, in contrast to those of the allylic alcohols, in low but opposite diastereoselectivity. The configuration of diastereomeric epoxy hydroperoxides were determined by NMR‐NOE experiments and chemical correlation.