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
1a
Greatrex BW.
Kimber MC.
Taylor DK.
Tiekink ERT.
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2003,
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4239
1b
Li DR.
Murugan A.
Falck JR.
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Am. Chem. Soc.
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130:
46
1c Kato H. inventors; JP 2008214276.
2a
Avery TD.
Taylor DK.
Tiekink ERT.
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Org. Chem.
2000,
65:
5531
2b
Palmer FN.
Taylor DK.
J.
Chem. Soc., Perkin Trans. 1
2000,
1323
The following patent shows the same
type of reaction in Table 1 without showing diastereoselectivity
of the reaction. See:
3a Kato H. inventors; JP 2008143880.
3b Kato H. inventors; JP 2008143881.
4a
Erdik E.
Tetrahedron
1992,
48:
9577
4b
Knochel P.
Millot N.
Rodriguez AL.
Tucker CE.
Org. React.
2001,
58:
417
5
Smith JG.
Synthesis
1984,
629
6 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.
7 From a ¹H NMR analysis, 4 was considered to have Z-configuration.
Alkenoic proton was detected at δ = 6.34 ppm.
See experimental procedure.
8a
Matsukawa S.
Funabashi Y.
Imamoto T.
Tetrahedron Lett.
2003,
44:
1007
8b
Tan K.-T.
Chng S.-S.
Cheng
H.-S.
Loh T.-P.
J. Am. Chem. Soc.
2003,
125:
2958
8c
Yanagisawa A.
Habaue S.
Yasue K.
Yamamoto H.
J. Am. Chem. Soc.
1994,
116:
6130
