Stannylformylation of vinylcyclopropanes accompanied by radical ring-opening

Tetrahedron Letters

Volumn 37, Issue 37, 1996, Pages 6729-6732

  Tsunoi, Shinji ^a   Ryu, Ilhyong ^a   Muraoka, Hideo ^a   Tanaka, Minoru ^a   Komatsu, Mitsuo ^a   Sonoda, Noboru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 16044367450     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)01453-0     Document Type: Article

References (14)

1. 1. Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570-7571. Also see a recent review: Ryu, I.; Sonoda, N. Angew. Chem. Int. Ed. Engl. 1996, 35, 1050-1066.
2. 1. Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570-7571. Also see a recent review: Ryu, I.; Sonoda, N. Angew. Chem. Int. Ed. Engl. 1996, 35, 1050-1066.
3. 2. (a) Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698.
4. (b) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5699-5707.
5. (c) Nonhebel, D. C. Chem. Soc. Rev. 1993, 347-359.
6. (d) Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
7. (b) Beckwith, A. L. J.; Bowry, V. W. J. Am. Chem. Soc. 1994, 116, 2710-2716.
8. (e) Feldman, K. S. Synlett 1995, 217-225.
9. 3. For radical-mediated hydrostannylation of vinylcyclopropanes, see: Ratier, M.; Pereyre, M. Tetrahedron Lett. 1976, 2273-2276.
10. 13C-NMR data, see: Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066-1081.
11. 5. For other synthetic utility of 1a, see: Ryu, I.; Ikura, K.; Tamura, Y.; Maenaka, J.; Ogawa, A.; Sonoda, N. Synlett 1994, 941-942.
12. 6. For the use of 1a for radical polymerization, see: Mizukami, S.; Kihara, N.; Endo, T. J. Am. Chem. Soc. 1994, 116, 6453-6454.
13. 24O m/z 316.1827, found, 316.1831. The regiochemistry of double bond was confirmed based on NOE experiments, in which an enhancement (2.8%) of vinyl proton signal (5.59 ppm) was observed when the ortho proton of phenyl group was irradiated. The chemical shift of two methine proton signals for minor isomer was observed at lower field (β: 3.14 and α: 3.51 ppm) compared with those of major isomer, supporting the major isomer being trans. 8. Higher reactivity of acyl radical to 1f relative to 1e can be explained by lower LUMO of 1f (LUMO of 1e: 1.02 eV, LUMO of 1f: 0.18 eV, by PM3).
14. 9. Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295-1297.