Abstract:
3-Alkanoylprop-2-en-1-ol derivatives were prepared stereoselectively
by ring-opening reaction of β,γ-epoxyketone with amines.
Key words
epoxide - amine - enone - rearrangement - alcohol
References and Notes
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The following patent shows the same
type of reaction in Table 1 without showing diastereoselectivity
of the reaction. See:
<A NAME="RU11908ST-3A">3a</A>
Kato H. inventors; JP 2008143880.
<A NAME="RU11908ST-3B">3b</A>
Kato H. inventors; JP 2008143881.
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Synthesis
1984,
629
<A NAME="RU11908ST-6">6</A>
The reaction was monitored by ¹H
NMR for 2 h using CD2Cl2 as solvent. Through
the whole reaction, Z-form was not detected
in the product.
<A NAME="RU11908ST-7">7</A>
From a ¹H NMR analysis, 4 was considered to have Z-configuration.
Alkenoic proton was detected at δ = 6.34 ppm.
See experimental procedure.
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