Collect. Czech. Chem. Commun.
     2000, 65, 741-756
  https://doi.org/10.1135/cccc20000741
  
Catalytic and Stoichiometric Lewis Acid Participation in Aldehyde Ene Cyclisations
D. Christopher Braddock and John M. Brown*
Dyson Perrins Laboratory, South Parks Rd., Oxford OX1 3QY, U.K.
References
1. Many aldol-type reactions of vinyl ethers and ketene acetals may follow an ene-pathway. In excluding these from the discussion we follow the inclinations of the original authors with regard to classification see, e.g.  D. J., Bolm C.: Angew. Chem., Int. Ed. Engl. 1995, 34, 1717.
<https://doi.org/10.1002/anie.199517171>
2a.  K., Shimizu M.: Chem. Rev. 1992, 92, 1021.
<https://doi.org/10.1021/cr00013a014>
2b.  K., Terada M., Narisawa S., Nakai T.: Synlett 1992, 255.
<https://doi.org/10.1055/s-1992-21333>
2c.  K.: Pure Appl. Chem. 1996, 68, 639; and earlier papers.
<https://doi.org/10.1351/pac199668030639>
3a.  K., Motoyama Y., Terada M.: Inorg. Chim. Acta 1994, 222, 71.
<https://doi.org/10.1016/0020-1693(94)03895-3>
3b.  M., Matsukawa S., Mikami K.: J. Chem. Soc., Chem. Commun. 1993, 327.
<https://doi.org/10.1039/c39930000327>
3c.  M., Mikami K.: J. Chem. Soc., Chem. Commun. 1994, 833.
<https://doi.org/10.1039/c39940000833>
3d.  M., Mikami K.: J. Chem. Soc., Chem. Commun. 1995, 2391.
<https://doi.org/10.1039/c39950002391>
3e.  K., Terada M., Narisawa S., Nakai T.: Org. Synth. 1993, 71, 14.
3f.  M., Sayo N., Mikami K.: Synlett 1995, 411.
<https://doi.org/10.1055/s-1995-4999>
3g.  K., Matsukawa S.: Tetrahedron Lett. 1994, 35, 3133.
<https://doi.org/10.1016/S0040-4039(00)76849-3>
3h.  D., Imma H., Nakai T.: Tetrahedron Lett. 1995, 36, 1861.
<https://doi.org/10.1016/0040-4039(95)00134-X>
3i.  K., Yoshida A., Matsumoto Y.: Tetrahedron Lett. 1996, 37, 8515.
<https://doi.org/10.1016/0040-4039(96)01954-5>
4a.  K., Yajima T., Terada M., Uchimaru T.: Tetrahedron Lett. 1993, 34, 7591.
<https://doi.org/10.1016/S0040-4039(00)60408-2>
4b.  K., Yajima T., Siree N., Terada M., Suzuki Y., Kobayashi I.: Synlett 1996, 837.
<https://doi.org/10.1055/s-1996-5630>
4c.  K., Yajima T., Takasaki T., Matsukawa S., Terada M., Uchimaru T., Maruta M.: Tetrahedron 1996, 52, 85.
<https://doi.org/10.1016/0040-4020(95)00862-3>
4d.  K., Yajima T., Siree N., Terada M., Suzuki Y., Takanishi Y., Takezoe H.: Synlett 1999, 1895.
<https://doi.org/10.1055/s-1999-2990>
5.  K., Yoshida A.: Synlett 1995, 29.
<https://doi.org/10.1055/s-1995-4878>
6a.  D. A., Johnson J. S., Burgey C. S., Campos K. R.: Tetrahedron Lett. 1999, 40, 2879.
<https://doi.org/10.1016/S0040-4039(99)00395-0>
6b.  D. A., Burgey C. S., Paras N. A., Vojkovsky T., Tregay S. W.: J. Am. Chem. Soc. 1998, 120, 5824.
<https://doi.org/10.1021/ja980549m>
6c.  M., Joergensen K. A.: J. Org. Chem. 1995, 60, 5757.
<https://doi.org/10.1021/jo00123a007>
7.  E. J., Barnes-Seeman D., Lee T. W., Goodman S. N.: Tetrahedron Lett. 1997, 38, 6513.
<https://doi.org/10.1016/S0040-4039(97)01517-7>
8a.  K., Ooi T., Yamamoto H.: J. Am. Chem. Soc. 1990, 112, 9011.
<https://doi.org/10.1021/ja00180a073>
8b.  T., Maruoka K., Yamamoto Y.: Tetrahedron 1994, 50, 6505.
<https://doi.org/10.1016/S0040-4020(01)89682-4>
8c. See also  J. A., Andersen M. W.: J. Org. Chem. 1992, 57, 5851.
<https://doi.org/10.1021/jo00048a016>
9.  K., Terada M., Sawa E., Nakai T.: Tetrahedron Lett. 1991, 32, 6571.
<https://doi.org/10.1016/0040-4039(91)80224-T>
10.  K., Koizumi Y., Osawa A., Terada M., Takayama H., Nakagawa K., Okano T.: Synlett 1999, 1899.
<https://doi.org/10.1055/s-1999-2989>
11.  P., Ahmed G., Srogl J., Malkov A. V., Steele J.: J. Org. Chem. 1999, 64, 2765.
<https://doi.org/10.1021/jo9821675>
12.  D. C., Hii K. K., Brown J. M.: Angew. Chem., Int. Ed. Engl. 1998, 37, 1720.
<https://doi.org/10.1002/(SICI)1521-3773(19980703)37:12<1720::AID-ANIE1720>3.0.CO;2-W>
13. Braddock D. C., Brown J. M.: J. Chem. Soc., Perkin Trans. 1, submitted, April 2000.
14. Perrin D. D., Armarego W. L. F., Perrin D. R.: Purification of Laboratory Chemicals. Pergamon, Oxford 1988.
15.  W. G., Backlawski L. M.: J. Org. Chem. 1976, 41, 1879.
<https://doi.org/10.1021/jo00872a047>
16.  A. R., Wolff S., Agosta W. C.: J. Am. Chem. Soc.  1986, 108, 3393.
17a.  A. J., Hennessey J. P., Jr., Johnson W. C., Jr., Loomis W. D.: Phytochemistry 1983, 22, 2227.
<https://doi.org/10.1016/S0031-9422(00)80152-1>
17b.  P., Massonneau V., Simonneaux G.: Tetrahedron 1988, 44, 1409.
<https://doi.org/10.1016/S0040-4020(01)85919-6>
18.  P. L.: J. Am. Chem. Soc. 1970, 92, 1397.
<https://doi.org/10.1021/ja00708a049>
19.  H. E., Liang W. C., Weeks P. D.: J. Org. Chem. 1974, 39, 3102.
<https://doi.org/10.1021/jo00935a009>
20.  B. B.: Acc. Chem. Res. 1980, 13, 426.
<https://doi.org/10.1021/ar50155a007>
21.  A. L.: Org. React. 1974, 2, 178.


