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Epoxidation of allylic hydroperoxides by dimethyldioxirane and peroxy acids

✍ Scribed by Abou-Elzahab, Mohamed ;Adam, Waldemar ;Saha-Möller, Chantu R.

Book ID
102903143
Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
661 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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