Chiral 6,7-dihydrooxepin-2(5H)-ones and the azepinone analogues: Conformation and diastereofacial selectivity in addition to the enones

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 633-636

  Sato, Masayuki ^a   Uehara, Fumiaki ^a   Aizawa, Koh Ichi ^a   Kaneko, Chikara ^a   Satoh, Shun Ichi ^b   Furuya, Toshio ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; OXEPINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030061834     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02219-8     Document Type: Article

References (17)

1. Feringa, B. L.; Lange de, B.; Jong de, J. C.; Lubben, M.; Faber, W.; Schudde, E. P. Pure and Appl. Chem. 1992, 64, 1865. For nitrogen heterocycles: Romo, D.; Meyers, A. I. Tetrahedron, 1991, 47, 9503. Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem.., 1992, 57, 1057.
2. Feringa, B. L.; Lange de, B.; Jong de, J. C.; Lubben, M.; Faber, W.; Schudde, E. P. Pure and Appl. Chem. 1992, 64, 1865. For nitrogen heterocycles: Romo, D.; Meyers, A. I. Tetrahedron, 1991, 47, 9503. Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem.., 1992, 57, 1057.
3. Feringa, B. L.; Lange de, B.; Jong de, J. C.; Lubben, M.; Faber, W.; Schudde, E. P. Pure and Appl. Chem. 1992, 64, 1865. For nitrogen heterocycles: Romo, D.; Meyers, A. I. Tetrahedron, 1991, 47, 9503. Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem.., 1992, 57, 1057.
4. Pirkle, W. H.; Adams, P. E. J. Org. Chem., 1980, 45, 4117. Takano, S.; Shimazaki, Y.; Sekiguchi, Y.; Ogasawara, K. Synthesis, 1989, 539.
5. Pirkle, W. H.; Adams, P. E. J. Org. Chem., 1980, 45, 4117. Takano, S.; Shimazaki, Y.; Sekiguchi, Y.; Ogasawara, K. Synthesis, 1989, 539.
6. Kaneko, C.; Sato, M.; Sasaki, J.; Abe, Y. J. Hetericycl. Chem., 1990, 27, 25. Sato, M.; Murakami, M.; Sunami, S.; Kaneko, C.; Furuya, T.; Kurihara, H. J. Am. Chem. Soc., 1995, 117, 4279.
7. Kaneko, C.; Sato, M.; Sasaki, J.; Abe, Y. J. Hetericycl. Chem., 1990, 27, 25. Sato, M.; Murakami, M.; Sunami, S.; Kaneko, C.; Furuya, T.; Kurihara, H. J. Am. Chem. Soc., 1995, 117, 4279.
8. Demuth, M.; Palomer, A.; Sluma, H.-D.; Dey, A. K.; Kruger, C.; Tsay, Y.-H. Angew. Chem. Int. Ed. Engl., 1986, 25, 117. Seebach, D.; Zimmermann, J.; Gysel. U.; Ziegler, R.; Ha, T.-K. J. Am. Chem. Soc., 1988, 110, 4763.
9. Demuth, M.; Palomer, A.; Sluma, H.-D.; Dey, A. K.; Kruger, C.; Tsay, Y.-H. Angew. Chem. Int. Ed. Engl., 1986, 25, 117. Seebach, D.; Zimmermann, J.; Gysel. U.; Ziegler, R.; Ha, T.-K. J. Am. Chem. Soc., 1988, 110, 4763.
10. Still, W. C.; Galynker, I. Tetrahedron, 1981, 37, 3981.
11. Sato, M.; Kuroda, H.; Kaneko, C.; Furuya, T. J. Chem. Soc., Chem. Commun., 1994, 687.
12. Busque, F.; Cid, P.; March, P.; Figueredo, M.; Font, J. Heterocycles, 1995, 40, 387.
13. 1H-NMR and IR) and combustion or high resolution mass spectral analytical data.
14. Full details of the crystal structure investigation of 8 and anti-10 have been deposited at the Cambridge Crystallographic Data Centre, Lensfield Road, UK.
15. MOPAC PM3 was implemended on a Tektronix CAChe workstation.
16. A similar rationalization has been proposed for diastereofacial selectivity in addition to chiral 6-membered cyclic enones such as 2-cyclohexen-1-ones and 5,6-dihydro-2(2H)-pyrones. See: Deslongchamp, P.; Stereoeletronic Effects in Organic Chemistry, Pergamon, Oxford, 1983, p.209. Takano, S.; Setoh, M.; Ogasawara, K., Tetrahedron: Asymmetry, 1992, 3, 533.
17. A similar rationalization has been proposed for diastereofacial selectivity in addition to chiral 6-membered cyclic enones such as 2-cyclohexen-1-ones and 5,6-dihydro-2(2H)-pyrones. See: Deslongchamp, P.; Stereoeletronic Effects in Organic Chemistry, Pergamon, Oxford, 1983, p.209. Takano, S.; Setoh, M.; Ogasawara, K., Tetrahedron: Asymmetry, 1992, 3, 533.