Diastereodifferentiating [4+2]-photocycloaddition of tegafur with naphthalene

Heterocycles

Volumn 72, Issue , 2007, Pages 691-695

  Ohkura, Kazue ^a   Sugaoi, Tatsuyuki ^a   Takahashi, Masayuki ^a   Seki, Koh ichi ^b  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

^b HOKKAIDO UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547830421     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-06-S(K)54     Document Type: Article

References (17)

1. Ohkura K., and Seki K. Photochem. Photobiol. 74 (2001) 385
2. Ohkura K., Uchiyama S., Aizawa K., Nishijima K., and Seki K. Heterocycles 57 (2002) 1403
3. Ohkura K., Sugaoi T., Nishijima K., Kuge Y., and Seki K. Tetrahedron Lett. 43 (2002) 3113
4. Ohkura K., Sugaoi T., Ishihara T., Aizawa K., Nishijima K., Kuge Y., and Seki K. Heterocycles 61 (2003) 377
5. Ohkura K., Ishihara T., Nakata Y., and Seki K. Heterocycles 62 (2004) 213
6. Ohkura K., Sugaoi T., Ishihara T., and Seki K. Heterocycles 64 (2004) 57
7. Ohkura K., Ishihara T., Takahashi H., Takechi H., and Seki K. Heterocycles 66 (2005) 143
8. Ohkura K., Ishihara T., Nishijima K., Diakur J., and Seki K. Chem. Pharm. Bull. 53 (2005) 258
9. Ohkura K., Ishihara T., Nishijima K., Diakur J.M., and Seki K. Heterocycles 69 (2006) 515
10. and references cited therein. Grosch B., and Bach T. Enantioselective Photocycloaddition Reaction in Solution. In: Horspool W., and Lenci F. (Eds). CRC Handbook of Organic Photochemistry and Photobiology (2004), CRC press, Boca Laton 6111-61114
11. Okada K., Samizo F., and Oda M. Tetrahedron Lett. 28 (1987) 3819
12. Adam W., and Prein M. Tetrahedron 51 (1995) 12583
13. Salamci E., Secen H., Sütbeyaz Y., and Balci M. J. Org. Chem. 62 (1997) 2453
14. 3) b: 1.90-2.04 (3H, m), 2.18-2.38 (1H, m,), 3.78 (1H, dd, J=2.5, 31.0 Hz), 3.94 (1H, dd, J =5.0,14.9 Hz), 4.19 (1H, dd,J = 7.7, 14.9 Hz), 4.41(1 H, dd, J=2.5, 6.3 Hz), 4.58 (1H, dd, J = 4.2, 5.9 Hz), 5.27 (1, dd, J = 5.0, 7.7 Hz), 6.66 (1H, dd, J = 5.9, 7.7 Hz,), 6.78 (1H, dd, J = 6.3, 7.7 Hz), 6.92 (1H, brs), 7.16-7.34 (4H, m). HRFAB-MS: Cacld for C 1 gH 1 g03N2F: 329.1302. Found: 329.1277.
15. 2. The final model with 3817 unique data used and 286 parameters varied, converged to values of R1=0.048 (for 2 741 data with 1>2 a (I) and R (R W) = 0.092 (0.142) (all data).
16. X-Ray Crystallography of 4a: The diffraction experiment was carried out using a colorless transparent prism with the dimensions 0.20 x 0.20 x 0.10 mm. A diffractometer RAXIS-IV (RIGAKU) imaging plate area detector was used with graphite-monochromated MoKa radiation ()t, = 0.71070 A) to obtain the following crystal data: C,8H»N203F Mr = 328.34., a =12.6892(7) A, b=1 8.4209(8)A, c = 6.8992(3) A, a = 98.534(2)°, ß = 90.2734(8)°, Y = 74.839(2)°, V =1538.3(1) A3, triclinic, P1, Z = 4, Dx = 1.418 glcm3. The final model with 6755 unique data used and 570 parameters varied, converged to values of R l = 0.058 (for 4198 data with I>2 a (I) and R (RW) = 0.088 (0.145) (all data).
17. Usuki A., Funasaka Y., Oka M., and Ichihashi M. Int. J. Dermatol 36 (1997) 604