1,3-Rearrangement of ketene-N,O-acetals

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3713-3716

  Suzuki, Tatsuo ^a   Inui, Masaharu ^a   Hosokawa, Seijiro ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ANION; CARBON; KETENE DERIVATIVE; LEWIS ACID;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHIRALITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037471459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00610-5     Document Type: Article

References (15)

1. Evans D.A., Ennis M.D., Mathre D.J. J. Am. Chem. Soc. 104:1982;1737-1738.
2. For examples: (a) Evans, D. A.; Bebder, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526; (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017; (c) Evans, D. A.; Bebder, S. L.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630; (d) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139; (e) Paquett, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
3. For examples: (a) Evans, D. A.; Bebder, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526; (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017; (c) Evans, D. A.; Bebder, S. L.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630; (d) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139; (e) Paquett, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
4. For examples: (a) Evans, D. A.; Bebder, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526; (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017; (c) Evans, D. A.; Bebder, S. L.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630; (d) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139; (e) Paquett, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
5. For examples: (a) Evans, D. A.; Bebder, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526; (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017; (c) Evans, D. A.; Bebder, S. L.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630; (d) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139; (e) Paquett, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
6. For examples: (a) Evans, D. A.; Bebder, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526; (b) Jones, T. K.; Reamer, R. A.; Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998-3017; (c) Evans, D. A.; Bebder, S. L.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630; (d) Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139; (e) Paquett, L. A.; Duan, M.; Konetzki, I.; Kempmann, C. J. Am. Chem. Soc. 2002, 124, 4257-4270.
7. Hosokawa S., Sekiguchi K., Enemoto M., Kobayashi S. Tetrahedron Lett. 41:2000;6429-6433.
8. Hosokawa S., Sekiguchi K., Hayase K., Hirukawa Y., Kobayashi S. Tetrahedron Lett. 41:2000;6435-6439.
9. Hosokawa S., Kobayashi S. J. Synth. Org. Chem. Jpn. 59:2001;1103-1108.
10. Braddock D.C., Brown J.M. Tetrahedron: Asymmetry. 11:2000;3591-3607.
11. For [3,3]-sigmatropic rearrangement of N-allyl-ketene-N,O-acetal: (a) Huche, M. Tetrahedron Lett. 1976, 17, 2607-2610; (b) Corbier, J.; Cresson, P.; Jelenc, P. C. R. Acad. Sci., Ser. C 1970, 270, 1890-1893.
12. For [3,3]-sigmatropic rearrangement of N-allyl-ketene-N,O-acetal: (a) Huche, M. Tetrahedron Lett. 1976, 17, 2607-2610; (b) Corbier, J.; Cresson, P.; Jelenc, P. C. R. Acad. Sci., Ser. C 1970, 270, 1890-1893.
13. 3 were not successful.
14. 3) δ 0.84 (d, 3H, J=7.0 Hz), 0.86 (t, 3H, J=7.0 Hz), 0.88 (d, 3H, J=7.0 Hz), 1.22-1.32 (m, 4H), 1.54 (s, 3H), 2.00 (q, 2H, J=6.7 Hz), 2.28-2.38 (m, 1H), 3.44 (d, 1H, J=8.8 Hz), 4.07 (d, 1H, J=8.8 Hz), 4.13 (dd, 1H, J=3.4, 8.9 Hz), 4.16 (t, 1H, J=8.9 Hz), 4.45-4.49 (m, 1H), 4.52 (s, 2H), 5.38 (td, 1H, J=6.7, 15.9 Hz), 5.75 (d, 1H, J=15.9 Hz), 7.26-7.32 (m, 5H).
15. Results concerning a γ-alkylation will be reported in due course.