Montmorillonite-mediated hetero-Diels–Alder reaction of alkenes and o-quinomethanes generated in situ by dehydration of o-hydroxybenzyl alcohols

Abstract

The intermolecular hetero-Diels–Alder reaction of in situ-generated o-quinomethanes and unactivated alkenes has been accomplished through a wet montmorillonite catalyst in a LiClO₄–MeNO₂ solution to give good yields of varied chromane skeletons.

References

1. T. Katada, S. Eguchi, T. Esaki and S. Sasaki, J. Chem. Soc., Perkin Trans. 1, 1984, 2649; S. K. Paknikar, K. P. Fondekar and R. Mayer, Natl. Prod. Lett., 1996, 8, 253.
2. D. A. Bolon, J. Org. Chem., 1970, 35, 3666; O. L. Chapman, M. R. Engel, J. P. Springer and J. C. Cardy, J. Am. Chem. Soc., 1971, 93, 6696; M. Cornia, L. Merlini and A. Zanarotti, Gazz. Chim. Ital., 1977, 107, 299.
3. J. P. Marino and S. L. Dax, J. Org. Chem., 1984, 49, 3672.
4. G. Cardillo, M. Orena, G. Porzi and S. Sandri, J. Chem. Soc., Chem. Commun., 1979, 836; W. K. Anderson, E. J. LaVoie and P. G. Whitkop, J. Org. Chem., 1974, 39, 881.
5. Y.-L. Mao and Y. Boekelheide, Proc. Natl. Acad. Sci. U.S.A., 1980, 77, 1732; T. Inoue, S. Inoue and K. Sato, Bull. Chem. Soc. Jpn., 1990, 63, 1062; T. Inoue, S. Inoue and K. Sato, Bull. Chem. Soc. Jpn., 1990, 63, 1647.
6. H. Weenen and M. H. H. Nkunya, J. Org. Chem., 1990, 55, 5107; V. S. Parmar, O. D. Tyagi, A. Malhotra, S. K. Singh, K. S. Bisht and R. Jain, Nat. Prod. Rep., 1994, 219.
7. E. L. Ghisalberti, Phytochemistry, 1996, 41, 7.
8. K. Chiba, J. Sonoyama and M. Tada, J. Chem. Soc., Chem. Commun., 1995, 1381; K. Chiba, J. Sonoyama and M. Tada, J. Chem. Soc., Perkin Trans. 1, 1996, 1435; K. Chiba, T. Arakawa and M. Tada, Chem. Commun., 1996, 1763; K. Chiba, T. Arakawa and M. Tada, J. Chem. Soc., Perkin Trans. 1, 1998, 17, 2939; K. Chiba, Y. Yamaguchi and M. Tada, Terahedron Lett., 1998, 39, 9035.