Stereoselective preparation of 3-alkanoylprop-2-en-1-ol derivatives

Synlett

Volumn , Issue 5, 2009, Pages 0724-0726

  Sada, Mutsumi ^a   Ueno, Shizue ^a   Asano, Keisuke ^a   Nomura, Kenichi ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Alcohol; Amine; Enone; Epoxide; Rearrangement

Indexed keywords

EID: 62349097584     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087930     Document Type: Article

References (15)

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2. (b) Li, D. R.; Murugan, A.; Falck, J. R. J. Am. Chem. Soc. 2008, 130, 46.
3. (c) Kato, H. JP 2008214276, 2008.
4. (a) Avery, T. D.; Taylor, D. K.; Tiekink, E. R. T. J. Org. Chem. 2000, 65, 5531.
5. (b) Palmer, F. N.; Taylor, D. K. J. Chem. Soc., Perkin Trans. 1 2000, 1323.
6. The following patent shows the same type of reaction in Table 1 without showing diastereoselectivity of the reaction. See: (a) Kato, H. JP 2008143880, 2008.
7. (b) Kato, H. JP 2008143881, 2008.
8. (a) Erdik, E. Tetrahedron 1992, 48, 9577.
9. (b) Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Org. React. 2001, 58, 417.
10. Smith, J. G. Synthesis 1984, 629.
11. 2 as solvent. Through the whole reaction, Z-form was not detected in the product.
12. 1H NMR analysis, 4 was considered to have Z-configuration. Alkenoic proton was detected at δ = 6.34 ppm. See experimental procedure.
13. (a) Matsukawa, S.; Funabashi, Y.; Imamoto, T. Tetrahedron Lett. 2003, 44, 1007.
14. (b) Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
15. (c) Yanagisawa, A.; Habaue, S.; Yasue, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6130.