Selective cleavage of the trisubstituted cyclopropanes via cyclopropylcarbinyl radical fragmentation

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6817-6820

  Takekawa, Yuki ^a   Shishido, Kozo ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Cyclopropanes; Enzyme reactions; Enzymes; Lignans; Radical reactions; Radicals

Indexed keywords

CYCLOPROPANE DERIVATIVE; ENZYME; LIGNAN; RADICAL;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ENZYME MECHANISM; OPTICAL ROTATION; SYNTHESIS;

EID: 0033543631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01366-0     Document Type: Article

References (21)

1. For a review: Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115.
2. For recent reports: (a) Simakov, P. A.; Martinez, F. N.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1998, 63, 1226-1232.
3. (b) Engel, P. S.; He, S.-L.; Banks, J. T.; Ingold, K. U.; Lusztyk, J. J. Org. Chem. 1997, 62, 1210-121 4.
4. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
5. Hudlicky, T.; Reddy, D. B.; Govindan, S. V.; Kulp, T.; Still, B.; Sheth, J. P. J. Org. Chem. 1983, 48, 3422-3428.
6. 2=OH).
7. (a) Faber, K. Biotransformations in Organic Chemistry; 3rd Ed.; Springer: Berlin, 1997.
8. (b) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826.
9. For the desymmetrization of cyclopropane derivatives: (a) Itoh, T.; Mitsukura, K.; Furutani, M. Chem. Lett. 1998, 903-904.
10. (b) Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1991, 47, 1215-1230.
11. (c) Sabbioni, G.; Jones, B. J. Org. Chem. 1987, 52, 4565-4570.
12. (d) Ader, U.; Breitgoff, D.; Klein, P.; Laumen, K. E.; Schneider, M. P. Tetrahedron Lett. 1989, 30, 1793-1796.
13. (e) Jakovac, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. J. Am. Chem. Soc. 1892, 104, 4659-4665.
14. R) of the protons.
15. Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853-1856.
16. Because of the lability of 11a, its optical purity could not be determined at this stage.
17. (a) Bode, J. W.; Doyle, M. P.; Protopopova, M. N.; Zhou, Q.-L. J. Org. Chem. 1996, 61, 9146-9155.
18. (b) Charlton, J. L.; Chee, G.-L. Can. J. Chem. 1997, 75, 1076-1083.
19. (c) Honda, T.; Kimura, N.; Sato, S.; Kato, D.; Tominaga, H. J. Chem. Soc., Perkin Trans. 1 1994, 1043-1046.
20. (d) Tomioka, K.; Koga, K. Tetrahedron Lett. 1979, 3315-3318.
21. (e) Yoda, H.; Naito, S.; Takabe, K.; Tanaka, N.; Hosoya, K. Tetrahedron Lett. 1990, 31, 7623-7626.