Regioselective formation of 2-alkoxyoxetanes in the photoreaction of aromatic carbonyl compounds with β,β-dimethyl ketene silyl acetals: notable solvent and silyl group effects

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Manabu Abe, Yasuo Shirodai and Masatomo Nojima


Abstract

Regioselective formation of 2-alkoxyoxetanes 3 was achieved in the photoreactions of aromatic ketones 2 with electron-rich ketene silyl acetals 1. In the photoreactions, the silyl-migration adduct 5 was also formed together with the oxetane 3. The product ratios of 3 and 5 were largely dependent on the solvent used and the silyl group of 1. The exclusive formation of 2-alkoxyoxetanes 3 was controlled by proper choice of the solvent and silyl group.


References

  1. (a) S. L. Schreiber, A. H. Hoveyda and H. Wu, J. Am. Chem. Soc., 1983, 105, 660 CrossRef CAS; (b) S. L. Schreiber and K. Satake, J. Am. Chem. Soc., 1983, 105, 6723 CrossRef; (c) J. A. Porco and S. L. Schreiber, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon Press, New York, 1991, vol. 5, pp. 168–188 Search PubMed; (d) A. Zamojeski and S. Jarosz, Tetrahedron Lett., 1982, 38, 1447; (e) M. Abe, M. Ikeda and M. Nojima, J. Chem. Soc., Perkin Trans. 1, following paper in this issue Search PubMed.
  2. (a) For review, see: A. G. Griesbeck, in Organic Photochemistry and Photobiology, eds. W. M. Horspool and P. Song, CRC Press, New York, 1995, pp. 522–535 Search PubMed; (b) C. Rivas and F. Vargas, in Organic Photochemistry and Photobiology, eds. W. M. Horspool and P. Song, CRC Press, New York, 1995, pp. 536–549 Search PubMed; (c) A. G. Griesbeck, in Organic Photochemistry and Photobiology, eds. W. M. Horspool and P. Song, CRC Press, New York, 1995, pp. 550–559 Search PubMed; (d) H. A. J. Carless, in Organic Photochemistry and Photobiology, eds. W. M. Horspool and P. Song, CRC Press, New York, 1995, pp. 560–569 Search PubMed; (e) H. A. J. Carless, in Synthetic Organic Photochemistry, ed. W. M. Horspool, Plenum Press, New York, 1984, pp. 425–488 Search PubMed; (f) N. J. Turro, Modern Molecular Photochemistry, The Benjamin/Cummings Publishing Co., Inc., Menlo Park, 1978, pp. 432–452 Search PubMed.
  3. (a) S. H. Schroeter and C. M. Orlando, J. Org. Chem., 1969, 34, 1181 CrossRef; (b) N. J. Turro and P. A. Wriede, J. Am. Chem. Soc., 1970, 92, 320 CrossRef CAS; (c) S. H. Schroeter, J. Chem. Soc., Chem Commun., 1969, 12 RSC; (d) T. Bach, Tetrahedron Lett., 1991, 32, 7037 CrossRef CAS; (e) H. A. Carless and D. J. Haywood, J. Chem. Soc., Chem. Commun., 1980, 1067 RSC; (f) A. G. Griesbeck and S. Stadtmüller, J. Am. Chem. Soc., 1990, 112, 1281 CrossRef CAS.
  4. S. Fukuzumi, M. Fujita, J. Otera and Y. Fujita, J. Am. Chem. Soc., 1992, 114, 10 271 CrossRef CAS.
  5. M. Abe, M. Ikeda, Y. Shirodai and M. Nojima, Tetrahedron Lett., 1996, 37, 5901 CrossRef CAS.
  6. S. Fukuzumi, T. Okamoto and J. Otera, J. Am. Chem. Soc., 1994, 116, 5503 CrossRef CAS.
  7. S. L. Murov, I. Carmichael and G. L. Hug, Handbook of Photochemistry, Marcel Dekker, Inc., New York, 1993, p. 75 Search PubMed.
  8. J. Mattay and J. Runsink, J. Org. Chem., 1985, 50, 2815 CrossRef CAS.
  9. C. G. Swain, M. S. Swain, A. L. Powell and S. Alunni, J. Am. Chem. Soc., 1983, 105, 502 CrossRef CAS.
  10. A. Takuwa, J. Shiiji and Y. Nishigaichi, Tetrahedron Lett., 1993, 34, 3457 CrossRef CAS.
  11. This work; see Experimental section.
  12. (a) A. Weller, Pure Appl. Chem., 1968, 16, 115 CrossRef CAS; (b) D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259 CAS.
  13. P. J. Wagner, R. J. Truman, A. E. Puchalski and R. Wake, J. Am. Chem. Soc., 1986, 108, 7727 CrossRef CAS.
  14. (a) A. G. Myers and K. L. Widdowson, J. Am. Chem. Soc., 1990, 112, 9672 CrossRef CAS; (b) A. G. Myers, K. L. Widdowson and P. J. Kukkola, J. Am. Chem. Soc., 1992, 114, 2765 CrossRef CAS; (c) A. G. Myers, S. E. Kephart and H. Chen, J. Am. Chem. Soc., 1992, 114, 7922 CrossRef CAS; (d) P. M. Bodnar, W. S. Palmer, J. T. Shaw, J. H. Smitrovich, J. D. Sonnenburg, A. L. Presley and K. A. Woerpel, J. Am. Chem. Soc., 1995, 117, 10 575 CrossRef CAS; (e) S. E. Denmark, S. B. D. Winter, X. Su and K.-T. Wong, J. Am. Chem. Soc., 1996, 118, 7404 CrossRef CAS.
  15. EDA complex of silyl enol ether, see R. Rathone and J. K. Kochi, J. Org. Chem., 1996, 61, 627 Search PubMed.
  16. (a) J. P. Dinnocenzo, S. Farid, J. I. Goodman, I. R. Gold, W. P. Todd and S. L. Mattes, J. Am. Chem. Soc., 1989, 111, 8973 CrossRef CAS; (b) K. P. Dockery, J. P. Dinnocenzo, S. Farid, J. L. Goodman and W. P. Todd, J. Am. Chem. Soc., 1997, 119, 1876 CrossRef CAS.
  17. (a) J. Mattay, J. Gersdorf and K. Buchkremer, Chem. Ber., 1987, 120, 307 CrossRef CAS; (b) J. Gersdorf, J. Mattay and H. Görner, J. Am. Chem. Soc., 1987, 109, 1203 CrossRef CAS; (c) J. Santamaria, in Photoinduced Electron Transfer, eds. M. A. Fox and M. Chanon, Elsevier, New York, 1988, Part C, pp. 483–540 Search PubMed.
  18. R. E. Ireland, P. Wipf and J. D. Armstrong, J. Org. Chem., 1991, 56, 650 CrossRef CAS.
  19. (a) L. Miller, G. D. Nordblom and E. A. Mayeda, J. Org. Chem., 1972, 37, 916 CrossRef CAS; (b) K. Yoshida, in Electrooxidation in Organic Chemistry, Krieger Publishing Company, Malabar, FL, 1993, pp. 43–44 Search PubMed.
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