A stereoselective and novel approach to the synthesis of 1,3-diols: simple control of diastereoselectivity

Abstract

Complete control of simple diastereoselectivity in the synthesis of 1,3-diols was realized through the use of a one-pot aldol addition and reduction process.

References

1. K. Tamao, T. Nakajima, R. Sumiya, H. Arai, N. Higuchi and Y. Ito, J. Am. Chem. Soc., 1986, 108, 6090.
2. A. F. Houri, M. T. Didiuk, Z. Xu, N. R. Horan and A. H. Hoveyda, J. Am. Chem. Soc., 1993, 115, 6614.
3. W. R. Roush, K. Ando and A. D. Palkowitz, J. Am. Chem. Soc., 1990, 112, 6348.
4. R. Menicagli, C. Malanga, M. Dell'Innocenti and L. Lardicci, J. Org. Chem., 1987, 52, 5700.
5. H. Sacha, D. Waldmüller and M. Braun, Chem Ber., 1994, 127, 1959 and references cited therein.
6. R. Mahrwald, Chem. Ber., 1995, 128, 919; R. Mahrwald and B. Gündogan, J. Am. Chem. Soc., 1998, 120, 413; R. Mahrwald, GIT Fachz. Lab., 1996, 40, 43.
7. R. Mahrwald and B. Gündogan, Tetrahedron Lett., 1997, 38, 4543; R. Mahrwald, B. Costisella and B. Gündogan, Synthesis, 1998, 262.
8. W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz and R. J. Haltermann, J. Am. Chem. Soc., 1990, 112, 6339; S. G. Davies, A. J. Edwards, G. B. Evans and A. A. Mortlock, Tetrahedron, 1994, 50, 6621.
9. C. M. Chan, J. M. Chong and K. Kousha, Tetrahedron, 1994, 50, 2703; R. A. Pilli and K. Z. de Andrade, Synth. Comm., 1994, 24, 233.
10. H. Maehr, R. Yang, L. N. Hong, C. M. Liu, M. H. Hatada and L. J. Torado, J. Org. Chem., 1989, 54, 3816; Y. Mori, M. Asai, J. Kawade and H. Furukawa, Tetrahedron, 1995, 51, 5315.
11. R. O. Duthaler, P. Herold, S. Wyler-Helfer and M. Riedicker, Helv. Chim. Acta, 1990, 73, 659; R. Baker, J. C. Head and C. J. Swain, J. Chem. Soc., Perkin Trans. 1, 1988, 85; L. Domon, F. Vogeleisen and D. Uguen, Tetrahedron Lett., 1996, 37, 2773.
12. M. Honda, T. Katsuki and M. Yamaguchi, Tetrahedron Lett., 1984, 25, 3857.