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Synlett 2009(5): 724-726
DOI: 10.1055/s-0028-1087930
DOI: 10.1055/s-0028-1087930
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Preparation of 3-Alkanoylprop-2-en-1-ol Derivatives
Further Information
Received
10 November 2008
Publication Date:
24 February 2009 (online)
Publication History
Publication Date:
24 February 2009 (online)
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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
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1a
Greatrex BW.Kimber MC.Taylor DK.Tiekink ERT. J. Org. Chem. 2003, 68: 4239 -
1b
Li DR.Murugan A.Falck JR. J. Am. Chem. Soc. 2008, 130: 46 -
1c
Kato H. inventors; JP 2008214276. -
2a
Avery TD.Taylor DK.Tiekink ERT. J. 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:
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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 -
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
References and Notes
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.
7From a ¹H NMR analysis, 4 was considered to have Z-configuration. Alkenoic proton was detected at δ = 6.34 ppm. See experimental procedure.