Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction

Tetrahedron Letters

Volumn 46, Issue 18, 2005, Pages 3245-3248

  Inui, Masaharu ^a   Hosokawa, Seijiro ^a,b   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b WASEDA UNIVERSITY   (Japan)

Author keywords

1,5 Rearrangement; Lewis acid; Vinylketene N,O acetal; Vinylogous Ferrier reaction

Indexed keywords

ACETAL DERIVATIVE; DICHLOROMETHANE; KETONE DERIVATIVE; LEWIS ACID; VINYL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 17044427098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.050     Document Type: Article

References (14)

1. T. Suzuki, M. Inui, S. Hosokawa, and S. Kobayashi Tetrahedron Lett. 44 2003 3713 3716
2. R.J. Ferrier, and S. Middleton Chem. Rev. 93 1993 2779 2831
3. See for stereo- and regioselective α-alkylation of α,β-unsaturated chiral imides from our laboratory: S. Hosokawa, K. Sekiguchi, M. Enemoto, and S. Kobayashi Tetrahedron Lett. 41 2000 6429 6433
4. S. Hosokawa, and S. Kobayashi J. Synth. Org. Chem. Jpn. 59 2001 1103 1108
5. T. Abe, T. Suzuki, K. Sekiguchi, S. Hosokawa, and S. Kobayashi Tetrahedron Lett. 44 2003 9303 9305
6. Reactions in other solvents such as chloroform-dichloromethane (1:1) and hexane-dichloromethane (1:1) were also examined to obtain poor results
7. 3 were not effective in terms of yield and selectivity
8. H. Nagaoka, and Y. Kishi Tetrahedron 37 1981 3873 3888
9. See also: S. Shirokawa, M. Kamiyama, T. Nakamura, M. Okada, A. Nakazaki, S. Hosokawa, and S. Kobayashi J. Am. Chem. Soc. 126 2004 13604 13605
10. S. Hosokawa, T. Ogura, H. Togashi, and K. Tatsuta Tetrahedron Lett. 46 2005 333 337
11. M.J. Aurell, S. Gil, R. Mestres, M. Parra, and L. Parra Tetrahedron 54 1998 4357 4366
12. I. Paterson, and L.G. Price Tetrahedron Lett. 22 1981 2833 2836
13. P.M. Savu, and J.A. Katzenellenbogen J. Org. Chem. 46 1981 239 250
14. 1H NMR spectra (600 MHz) were recorded on a Bruker AVANCE 600 spectrometer. Each product is distinguishable by the proton either at the 4-position of oxazolidin-2-one or the vinylproton at the β-position