3-Thiabicyclo-[3,3,0]-oct-5-en-7-ones by DMSO/DMS Promoted Intramolecular Pauson-Khand Reaction

Synlett

Volumn 1997, Issue 2, 1997, Pages 205-207

  Stumpf, Andreas ^a,b   Jeong, Nakcheol ^a   Sunghee, Hwang ^a  

^a Hanhyo Institutes of Technology   (South Korea)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002597035     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-741     Document Type: Article

References (17)

1. Pauson, P. L. Tetrahedron 1985, 41, 5855. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, E. M. J.Chem.Soc., Perkin Trans. 1973, 1, 975.
2. Pauson, P. L. Tetrahedron 1985, 41, 5855. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, E. M. J.Chem.Soc., Perkin Trans. 1973, 1, 975.
3. Schore, N. E. Org. React. 1991, 40, 1.
4. Schore, N. E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds; Pergamon Press: Oxford, 1991, Vol. 5, p. 1037.
5. For some recent applications of the PKR in natural product synthesis, see: Bernardes, V.; Kann, N.; Riera, A.; Pericas, M. A.; Greene, A. E. J.Org.Chem. 1995, 60, 6670. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J.Am.Chem.Soc. 1994, 116, 5505. Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651. Rowley, E. G.; Schore, N. E. J.Org.Chem. 1992, 57, 6853.
6. For some recent applications of the PKR in natural product synthesis, see: Bernardes, V.; Kann, N.; Riera, A.; Pericas, M. A.; Greene, A. E. J.Org.Chem. 1995, 60, 6670. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J.Am.Chem.Soc. 1994, 116, 5505. Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651. Rowley, E. G.; Schore, N. E. J.Org.Chem. 1992, 57, 6853.
7. For some recent applications of the PKR in natural product synthesis, see: Bernardes, V.; Kann, N.; Riera, A.; Pericas, M. A.; Greene, A. E. J.Org.Chem. 1995, 60, 6670. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J.Am.Chem.Soc. 1994, 116, 5505. Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651. Rowley, E. G.; Schore, N. E. J.Org.Chem. 1992, 57, 6853.
8. For some recent applications of the PKR in natural product synthesis, see: Bernardes, V.; Kann, N.; Riera, A.; Pericas, M. A.; Greene, A. E. J.Org.Chem. 1995, 60, 6670. Jamison, T. F.; Shambayati, S.; Crowe, W. E.; Schreiber, S. L. J.Am.Chem.Soc. 1994, 116, 5505. Veretenov, A. L.; Koltun, D. O.; Smit, W. A.; Strelenko, Y. A. Tetrahedron Lett. 1995, 36, 4651. Rowley, E. G.; Schore, N. E. J.Org.Chem. 1992, 57, 6853.
9. Cobaltcarbonylsulfide-complexes have been synthesized previously and been shown to be stable. M.E. Krafft, I. L. Scott, R. H. Romero, S. Feibelmann, C. E. Van Pelt J.Am.Chem.Soc. 1993, 115, 7199.
10. Berkessel, A. J.Org.Chem. 1989, 54, 1685.
11. 13C-NMR at 75 MHz, Bruker. 1H-NMR of 4 (CDCl3): 8 2.22 (dd, J = 3.0, 8.3 Hz, IH), 2.54 (dd, J= 11.2, 10.2Hz, IH), 2.73 (dd, J = 6.4, 18.3Hz, lH),3.16(dd, J = 10.0, 7.9 Hz, IH), 3.32 (m, IH), 3.78 (s, 2H), 6.03 (s, IH). 13C-NMR (CDCl3): 30.13, 34.69, 41.83, 48.10, 126.87, 183.28, 209.46. 1H-NMR of entry 3 in Table 1 (CDCl1): 6 1.54 (dd, J = 5.5, 6.7 Hz, 3H), 2.24 (dd, J = 2.5, 2.5 Hz, IH), 2.56 (m, 1 H), 2.69 (dd, J = 2.0, 6.5 Hz, 0.5H), 2.75 (dd. J = 2.1, 6.5 Hz, 0.5H), 3.16 (dd, J = 10.3, 18.7 Hz, 0.5H), 3.19 (dd, J = 10.2, 18.2 Hz, 0.5H), 3.48 (m, IH), 4.23 (q, J = 7.0 Hz, 0.5H), 4.26 (q, J = 7.0 Hz, 0.5H), 5.98 (t, J = 1.8 Hz. 0.5H), 5.97 (q, J = 0.8 Hz, 0.5H). 1H-NMR of entry 4 in Table 1 (CDCl3): ô1.04 (dd, J = 7.4,7.3 Hz, 0.6H), 1.22(dd, J = 7.4, OHz, 2.4H), 1.61 (m, 0.4H), 1.78(m, 1.6H), 2.23 (dd, J = 2.8, 18.4 Hz, 0.8H), 2.25 (dd, J = 2.8, 18.4 Hz, 0.2H), 2.53 (dd, J = 11.0, 10.2 Hz, IH), 2.67 (dd, J = 6.3, 18.3Hz, IH), 3.14 (dd, J = 10.0, 8.1 Hz, IH), 3.48 (m, IH), 4.06 (t, J = 7.4 Hz, 0.8 Hz, 0.8H), 4.2 (m, 0.2H), 5.99 (s, IH). 1H-NMR of entry S in Table 1 (CDCI3): O 2.21 (dd, J = 2.6, 18.4 Hz, IH), 2.48 (dd, J= 10.9, 10.0 Hz, IH)1 2.76 (dd, J = 6.3, 18.4Hz, IH), 3.13-3.33 (m, 6H), 3.80 (dd, J= 16.0, 47.9Hz, 2H), 5.11-5.24 (m, 2H), 5.74-5.89 (m, IH). 1H-NMROf entry 6 in Table 1 (CDCl3): ô1.43 (d, J = 7.2, 1.65H), 1.48 (d, J = 7.2 Hz, 1.35H), 1.52(d,J = 7.1 Hz, 1.65H), 1.57 (d,J = 7.1 Hz, 1.35H), 2.18 (t, J = 3.0 Hz, 0.45H), 2.25 (t, J = 3.0 Hz, 0.55H), 2.41-2.50 (m, IH), 2.75 (dd, J = 6.5, 18.5Hz, tH), 3.02-3.24 (m, 3H), 3.39 (m, IH), 3.83 (q, J = 7.2 Hz, 0.45H), 3.90 (q, J = 7.2 Hz, 0.55H), 4.38 (q, J = 6.8 Hz, 0.45H), 4.72 (q, J = 6.9 Hz, 0.55H), 5.04-5.17 (m, 2H), 5.71-5.88 (m, IH).
12. Smit, W. A.; Gybin, A. S.; Shashkov, A. S.; Strychkov, Y.T.; Kyz'mina, L. G.; Mikaelian, G. S.; Caple, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241.
13. Jeong, N.; Chung, Y. K.; Lee, B. Y; Lee, S. H.; Yoo, S.-E. Synlett 1991, 204.
14. Jeong, N.; Yoo, S.-E.; Lee, S. H.; Chung, Y. K. Tetrahedron Lett. 1991, 32, 2137.
15. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220.
16. 3): 35.06, 41.90, 42.21, 45.58, 46.37, 118.47, 126.49, 134.26, 185.76, 209.37.
17. 3): 14.37, 21.37, 23.88, 27.51, 40.98, 42.29, 43.35, 43.75, 49.99, 53.65, 71.68. GC-MS 169.15 (M-1, 3.7%) calc. 170.29.