Stereoselective synthesis of (E)- and (Z)-enol ethers from β-amino aldehydes

Archives of Pharmacal Research

Volumn 30, Issue 6, 2007, Pages 695-700

  In, Jin Kyung ^a   Lee, Mi Sung ^a   Lee, Min Woo ^a   Kwak, Jae Hwan ^a   Lee, Heesoon ^a   Jin, Tae Hong ^a   Chung, Yongseog ^a   Choi, Yongseok ^b   Jung, Jae Kyung ^a  

^a Chungbuk National University   (South Korea)

^b Korea University   (South Korea)

Author keywords

Building block; Enol ether; amino aldehyde

Indexed keywords

EID: 34447102234     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02977630     Document Type: Article

References (14)

1. Brownbridge, P., Silyl enol ethers in synthesis 1. Synthesis, 1-28 (1983).
2. Castro, A. M. M., Claisen rearrangement over the past nine decades. Chem. Rev., 104, 2939-2002 (2004).
3. Deiters, A., Chen, K., Eary, C. T., and Martin, S. F., Biomimetic entry to the sarpagan family of indole alkaloids: Total synthesis of (+)-Geissoschizine and (+)-N-Methylvellosimine. J. Am. Chem. Soc., 125, 4541-4550 (2003).
4. Fleming, I., Barbero, A., and Walter, D., Stereochemical control in organic synthesis using silicon-containing compounds. Chem. Rev., 97, 2063-2192 (1997).
5. Hydrio, J., Van de Weghe, P., and Collin, J., Easy preparation of enoxysilanes from aldehydes and ketones catalyzed by samarium diiodide. Synthesis, 68-72 (1997).
6. Ishino, Y., Kita, Y., Maekawa, H., Ohno, T., Yamasaki, Y., Mxiyata, T., and Nishiguchi, I., Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride. Tetrahedron Lett., 40, 1349-1352 (1999).
7. Jung, J.-K., Choi, N.-S., and Suh, Y.-G., Functional divergence oriented synthesis of azoninones as the key intermediates for bioactive indolizidine alkaloids analogs. Arch. Pharm. Res., 27, 985-989 (2004).
8. Liu, M. and Sibi, M. P., Recent advances in the steroselective synthesis of β-amino acid. Tetrahedron, 58, 7991-8035 (2002).
9. Maeda, K., Shinokubo, H., Oshima, K., and Utimoto, K., Stereoselective synthesis of allyl vinyl ethers from silyl enol ethers. J. Org. Chem., 61, 2262-2263 (1996).
10. Matthews, J. L., Braun, C., Guibourdenche, C., Overhand, M., and Seebach, D., In Enantioselective Synthesis of β-Amino Acids, Ed. Juaristi, E., Wiley, New York, 105-126 (1996).
11. Ohmura, T., Yamamoto, Y., and Miyaura, N., Stereoselective synthesis of silyl enol ethers via the iridium-catalyzed isomerization of allyl silyl ethers. Organometallics, 18, 413-416 (1999).
12. Park, H.-G., Kim, D.-H., Yoo, M.-S., Park, M.-K., and Jew, S.-S., Practical regioselective synthetic method for (E)-enol ether. Tetrahedron Lett., 41, 4579-4582 (2000).
13. Smietana, M. and Mioskowski, C., Preparation of silyl enol ethers using (bistrimethylsilyl)acetamide in ionic liquids. Org. Lett., 3, 1037-1039 (2001)
14. Taniguchi, Y., Inanaga, J., and Yamaguchi, M., Use of 1,8-diazabicyclo[5.4.0]undec-7-ene in preparation of trimethylsilyl enol ethers and trimethylsilylacetylene. Bull. Chem. Soc. Jpn., 54, 3229-3230 (1981).