Tin-mediated Organic Reactions: a Practical Method for the Synthesis of β-Hydroxynitriles and β-Hydroxyketones

Abstract

In the presence of chlorotrimethylsilane, the tin mediated addition of bromoacetonitrile or α-bromacetophenone to aldehydes in THF gives β-hydroxynitriles or β-hydroxyketones in moderate to good yields.

References

1. (a) T. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207; (b) C. J. Li, Chem. Rev., 1993, 93, 2023.
2. J. Y. Zhou, X. B. Yao, Z. G. Chen and S. H. Wu, Synth. Commun., 1995, 25, 3081.
3. T. Mandai, J. Nokami and T. Yano, J. Org. Chem., 1984, 49, 172.
4. J. Y. Zhou, Z. G. Chen and S. H. Wu, J. Chem. Soc., Chem. Commun., 1994, 278.
5. H. Walmann, Synlett, 1990, 627.
6. T. Harada and T. Mukaiyama, Chem. Lett., 1982, 161, 467.
7. X. Gao, B. Z. Huang and S. H. Wu, Acta Chim. Sinica, 1991, 49, 827.
8. W. Schmid and G. M. Whitesides, J. Am. Chem. Soc., 1991, 113, 6674.
9. P. Sun and Y. Zhang, Synth. Commun., 1997, 27, 3175.
10. X. L. Hou, X. L. Zheng and L. X. Dai, Tetrahedron Lett., 1998, 39, 6949.
11. S. Inaba and R. D. Rieke, Tetrahedron Lett., 1985, 26, 155.
12. E. Hasegaya, K. Ishiyama, T. Horaguchi and T. Shimizu, J. Org. Chem., 1991, 56, 1631.
13. S. Araki and Y. Butsugan, Bull. Chem. Soc. Jpn., 1991, 64, 727.