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29844447225
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Jpn. Patent JP 06092950 A2, 1994
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Amino alcohols have been previously reported to promote, in stoichiometric amounts, the epoxidation of electron-deficient alkenes to racemic epoxides: Masahiko, Y.; Noboru, K.; Satomi, T. Jpn. Patent JP 06092950 A2, 1994.
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note
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The s-trans conformation of the enone moiety might be preferentially adopted in the epoxidation reaction, although a noncoplanar enone geometry cannot be excluded.
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29844454394
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note
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Activation of the enone via iminium ion formation is less reasonably expected to occur under these reaction conditions, given the unreactive nature of enone carbonyls and the absence of an acid catalyst.
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6344261942
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0000163641
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29844452499
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note
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1H NMR analysis of the crude reaction mixture showed no significant degradation of 2 under the reaction conditions.
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29844448720
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note
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The epoxidation of 4a with the tertiary N-benzyl L-prolinol under the usual conditions (rt, hexane, TBHP, 90 h) furnished traces of the epoxide.
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