A novel one-pot synthesis of cyanohydrin alkyl ethers from aldehydes catalyzed by iron(III) chloride

Chemistry Letters

Volumn 33, Issue 10, 2004, Pages 1324-1325

  Iwanami, Katsuyuki ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOHYDRIN; ETHER DERIVATIVE; IRON DERIVATIVE; SILANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 11844272000     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1324     Document Type: Article

References (23)

1. R. J. H. Gregory, Chem. Rev., 99, 3649 (1999); J.-M. Brunel and I. P. Holmes, Angew. Chem., Int. Ed., 43, 2752 (2004).
2. R. J. H. Gregory, Chem. Rev., 99, 3649 (1999); J.-M. Brunel and I. P. Holmes, Angew. Chem., Int. Ed., 43, 2752 (2004).
3. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
4. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
5. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
6. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
7. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
8. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
9. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
10. D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 1973, 55; D. A. Evans and J. K. Truesdale, Tetrahedron Lett., 49, 4929 (1973); S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 541; M. Golinski, C. P. Carolyn, and D. S. Watt, J. Org. Chem., 58, 159 (1993); Y. Yang, D. Wang, Synlett, 1997, 1379; P. Saravanan, R. V. Anand, and V. K. Singh, Tetrahedron Lett., 39, 3823 (1998); M. Bandini, P. G. Cozzi, P. Melchiorre, and A. Umani-Ronchi, Tetrahedron Lett., 42, 3041 (2001); N. Azizi and M. R. Saidi, Phosphorus, Sulfur Silicon Relat. Elem., 178, 2111 (2003).
11. S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 537; S.-K. Tian and L. Deng, J. Am. Chem. Soc., 123, 6195 (2001); S.-K. Tian, R. Hong, and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003).
12. S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 537; S.-K. Tian and L. Deng, J. Am. Chem. Soc., 123, 6195 (2001); S.-K. Tian, R. Hong, and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003).
13. S. Kobayashi, Y. Tsuchiya, and T. Mukaiyama, Chem. Lett., 1991, 537; S.-K. Tian and L. Deng, J. Am. Chem. Soc., 123, 6195 (2001); S.-K. Tian, R. Hong, and L. Deng, J. Am. Chem. Soc., 125, 9900 (2003).
14. H. Zhou, F.-X. Chen, B. Qin, X. Feng, and G. Zhangb, Synlett, 2004, 1077.
15. S. Hünig and R. Schaller, Angew. Chem., Int. Ed. Engl., 21, 36 (1982).
16. a) M. Okimoto and T. Chiba, Synthesis, 1996, 1188.
17. b) H. M. R. Hoffman, Z. M. Ismail, R. Hollwag, and A. R. Zein, Bull. Chem. Soc. Jpn., 63, 1807 (1990).
18. T. Watahiki, S. Ohba, and T. Oriyama, Org. Lett., 5, 2679 (2003).
19. T. Mukaiyama, T. Soga, and H. Takenoshita, Chem. Lett., 1989, 997.
20. T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 3rd ed., John Wiley & Sons, New York (1999), p 76.
21. T. Watahiki and T. Oriyama, Tetrahedron Lett., 43, 8959 (2002).
22. T. Watahiki, Y. Akabane, S. Mori, and T. Oriyama, Org. Lett., 5, 3045 (2003).
23. 4. α-(Benzyloxy)- phenylacetonitrile (135.2 mg, 98%) was isolated by thin-layer chromatography on silica gel.