Anomalous epoxide formation upon Wittig olefination with 1-iodoethyl triphenylphosphonium ylide

Synlett

Volumn , Issue 7, 1998, Pages 765-767

  Arimoto, Hirokazu ^a   Kaufman, Michael D ^b   Kobayashi, Kaoru ^b   Qiu, Yuping ^b   Smith III, Amos B ^b  

^a SHIZUOKA UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000908260     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1770     Document Type: Article

References (21)

1. Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011-12012.
2. Chen, J.; Wang, T.; Zhao, K. Tetrahedron Lett. 1994, 35, 2827-2828.
3. For related approaches to 2-iodo-2-alkenes, see: Shen, Y.; Gao, S. J. Chem. Soc. Perkin Trans. I 1995, 1331-1332 and references therein.
4. Su, D.-S.; Meng, D.; Bertinato, P.; Balog, A.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 757-759.
5. 13C NMR spectra, as well as appropriate parent ion identification by high resolution mass spectrometry.
6. 13C NMR (125 MHz, CDCl3) δ -3.99, -3.95, 14.5, 14.7, 18.4, 26.1, 33.5, 38.7, 44.5, 55.3, 72.5, 72.6, 76.5, 98.9, 113.7, 129.1, 131.0, 139.6, 159.1.
7. 2) δ -4.0, -3.8, 14.8, 15.3, 18.6, 26.3, 29.9, 32.3, 38.6, 48.5, 54.7, 72.7, 73.0, 77.1, 129.4, 131.4, 159.7. 205.9
8. 3) δ 0.04 (s, 3 H), 0.06 (s, 3 H), 0.88 (s, 9 H), 0.89 (d, J = 6.9 Hz, 3 H), 0.93 (d, J = 6.9 Hz, 3 H) 1.23 (d, J = 5.5 Hz, 3 H), 1.46 (ddq, J = 3.0, 9.6, 6.9 Hz, 1 H), 2.00 (m, 1 H), 2.76 (dd, J = 4.4, 9.5 Hz, 1 H), 3.06 (dq, J = 4.4, 5.5 Hz, 1 H), 3.22 (dd. J = 7.8, 9.0 Hz, 1 H), 3.55 (dd, J = 4.7, 9.0 Hz, 1 H), 3.77 (dd, J = 3.0, 6.6 Hz, 1 H), 3.78 (s, 3 H), 4.39 (d, J = 11.6 Hz, 1 H), 4.41 (d, J = 11.6 Hz, 1 H), 6.85 (br d, J = 8.6 Hz, 2 H), 7.24 (br d, J = 8.6 Hz, 2H).
9. 1H NMR coupling constants and NOE experiments. The stereochemistry of 6a was further established by preparation of 12 and then application of the Kakisawa-Trost NMR analysis; see: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
10. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374. (Chemical Equation Presented)
11. For reviews of the Wittig reaction, see: a) Vedejs, E.; Peterson, M. J. Advances in Carbanion Chemistry 1996, 2, 1-85.
12. b) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863-927.
13. Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
14. Corey, E. I.; Shulman, J. I.; Yamamoto, H. Tetrahedron Lett. 1970, 447-450.
15. Bestmann, H. J.; Zimmermann In Carbon-Carbon Bond Formation; Augustine, R. L., Ed.; M. Dekker: New York, 1979; Vol. 1, Chapter 3, p 357.
16. Quin, L. D.; Symmes, C., Jr.; Middlemas, E. D.; Lawson, F. J. Org. Chem. 1980, 45, 4688-4694.
17. CP = 2.6 Hz), 159.24 (C).
18. Lohse, P.; Loner, H.; Acklin, P.; Sternfeld, F.; Pfaltz, A. Tetrahedron Lett. 1991, 32, 615-618.
19. Satoh, T.; Horiguchi, K. Tetrahedron Lett. 1995, 36, 8235-8238.
20. An analogous bromoalkylidene has also been reported to give Z selective olefination; Smithers, R. H. J. Org. Chem. 1978, 43, 2833-2838.
21. αβ-Epoxysilanes have been prepared in a similar manner. See: Burford, C.; Cooke, F.; Ehlinger, E.; Magnus, P. J. Am. Chem. Soc. 1977, 99, 4536-4537.