Stereoselective Preparation of 3-Alkanoylprop-2-en-1-ol Derivatives

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. 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:
• 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 

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.