PhSH - (catalytic) KF as an efficient protocol for chemoselective ester O-alkyl cleavage under non-hydrolytic neutral condition

Chemistry Letters

Volumn , Issue 4, 1998, Pages 297-298

  Nayak, Mrinal K ^a   Chakraborti, Asit K ^b  

^a UNIVERSITY OF BURDWAN   (India)

^b NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032370642     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.297     Document Type: Article

References (34)

1. J. McMurry, Org. React., 24, 187 (1976).
2. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
3. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
4. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
5. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
6. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
7. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
8. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
9. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
10. A. Haslam, Tetrahedron, 36, 2409 (1989); C. J. Salomon, E. G. Mata, and O. A. Mascaretti, Tetrahedron, 49, 3691 (1993); T. W. Greene and P. G. M. Wuts, in "Protective Groups in Organic Synthesis," 2nd. Ed., John Wiley, New York (1991), p77; P. J. Koceinski, in "Protecting Groups," Georg Thieme Verlag, Stuttgart (1994); K. Jarowicki and P. J. Kocienski, Contemporary Organic Synthesis, 2, 316 (1995); Y. -C. Xu, E. Lebeau, and C. Walker, Tetrahedron Lett., 34, 6207 (1994); Y. -C. Xu, A. Bizuneh, and C. Walker, Tetrahedron Lett., 37, 455 (1996); W. -C. Chen, M. D. Vera, and M. M. Joullie, Tetrahedron Lett., 38, 4025 (1997); S. P. Chavan, P. K. Zubaidha, S. W. Dantale, A. Keshavaraja, A. V. Ramaswamy, and T. Ravindranathan, Tetrahedron Lett., 37, 237 (1996).
11. S. V. Ley and D. M. Mynett, Synlett., 1993, 793; L. V. Boisslier, M. Postel, and E. Bunnach, Tetrahedron Lett., 38, 2981 (1997).
12. S. V. Ley and D. M. Mynett, Synlett., 1993, 793; L. V. Boisslier, M. Postel, and E. Bunnach, Tetrahedron Lett., 38, 2981 (1997).
13. C. J. Salomon, E. G. Mata, and O. A. Mascaretti, J. Org. Chem., 59, 7259 (1994), C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Chem. Soc., Perkin Trans. I, 1996, 995; R. L. E. Furlan, E. G. Mata, and O. A. Mascaretti, Tetrahedron Lett., 37, 5229 (1997); Y. Kita, T. Ogawa, and K. Hatiyama, Chem. Abstr., 123, 169520p (1995); C. Goux, P. Lhoste, D. Shinou, and J. Muzart, Sulfur Lett., 18, 1 (1994).
14. C. J. Salomon, E. G. Mata, and O. A. Mascaretti, J. Org. Chem., 59, 7259 (1994), C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Chem. Soc., Perkin Trans. I, 1996, 995; R. L. E. Furlan, E. G. Mata, and O. A. Mascaretti, Tetrahedron Lett., 37, 5229 (1997); Y. Kita, T. Ogawa, and K. Hatiyama, Chem. Abstr., 123, 169520p (1995); C. Goux, P. Lhoste, D. Shinou, and J. Muzart, Sulfur Lett., 18, 1 (1994).
15. C. J. Salomon, E. G. Mata, and O. A. Mascaretti, J. Org. Chem., 59, 7259 (1994), C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Chem. Soc., Perkin Trans. I, 1996, 995; R. L. E. Furlan, E. G. Mata, and O. A. Mascaretti, Tetrahedron Lett., 37, 5229 (1997); Y. Kita, T. Ogawa, and K. Hatiyama, Chem. Abstr., 123, 169520p (1995); C. Goux, P. Lhoste, D. Shinou, and J. Muzart, Sulfur Lett., 18, 1 (1994).
16. C. J. Salomon, E. G. Mata, and O. A. Mascaretti, J. Org. Chem., 59, 7259 (1994), C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Chem. Soc., Perkin Trans. I, 1996, 995; R. L. E. Furlan, E. G. Mata, and O. A. Mascaretti, Tetrahedron Lett., 37, 5229 (1997); Y. Kita, T. Ogawa, and K. Hatiyama, Chem. Abstr., 123, 169520p (1995); C. Goux, P. Lhoste, D. Shinou, and J. Muzart, Sulfur Lett., 18, 1 (1994).
17. C. J. Salomon, E. G. Mata, and O. A. Mascaretti, J. Org. Chem., 59, 7259 (1994), C. J. Salomon, E. G. Mata and O. A. Mascaretti, J. Chem. Soc., Perkin Trans. I, 1996, 995; R. L. E. Furlan, E. G. Mata, and O. A. Mascaretti, Tetrahedron Lett., 37, 5229 (1997); Y. Kita, T. Ogawa, and K. Hatiyama, Chem. Abstr., 123, 169520p (1995); C. Goux, P. Lhoste, D. Shinou, and J. Muzart, Sulfur Lett., 18, 1 (1994).
18. P. A. Bartlett and W. S. Johnson, Tetrahedron Lett., 1970, 4459.
19. G I. Feutrill and R. N. Mirrington, Aust. J. Chem., 25, 1731 (1972).
20. T. R. Kelly, H. M. Dali, and W. -G. Tsang, Tetrahedron Lett., 1977, 3859.
21. N. Kornblum, L. Cheng, R. C. Krebber, M. V. Kestner, B. N. Newton, H. W. Pinnick, R. G. Smith, and P. A. Wade, J. Org. Chem., 41, 1560 (1976).
22. J. R. Beck, J. Org. Chem., 38, 4086 (1973).
23. A. J. Caruso, A. M. Colley, and G. L. Bryant, J. Org. Chem., 56, 862 (1991) and references cited therein.
24. P. S. Surdhar and D. A. Armstrong, J. Phys. Chem., 90, 5915 (1986).
25. J. R. Hwu, F. F. Wong, and M. -J. Shiao, J. Org. Chem., 57, 5254 (1992); M.-J. Shiao, L. -L. Lai, W. -S. Ku, P. -Y. Lin, and J. R. Hwu, J. Org. Chem., 58, 4742 (1993).
26. J. R. Hwu, F. F. Wong, and M. -J. Shiao, J. Org. Chem., 57, 5254 (1992); M.-J. Shiao, L. -L. Lai, W. -S. Ku, P. -Y. Lin, and J. R. Hwu, J. Org. Chem., 58, 4742 (1993).
27. J. W. G. Meissner, A. C. van der Laan, and U. K. Pandit, Tetrahedron Lett., 35, 2757 (1994).
28. M Ueki, H. Aoki, and T. Katoh, Tetrahedron Lett., 34, 2783 (1993).
29. M. E. Niyazymbetov, A. L. Laikhter, V. V. Semenov, and D. H. Evans, Tetrahedron Lett., 35, 3037 (1994); K. Tomioka, A. Muraoka, and M. Kanai, J. Org. Chem., 60, 6188 (1995), A. Ito, K. Konishi, and T. Aida, Tetrahedron Lett., 37, 2585 (1996)
30. M. E. Niyazymbetov, A. L. Laikhter, V. V. Semenov, and D. H. Evans, Tetrahedron Lett., 35, 3037 (1994); K. Tomioka, A. Muraoka, and M. Kanai, J. Org. Chem., 60, 6188 (1995), A. Ito, K. Konishi, and T. Aida, Tetrahedron Lett., 37, 2585 (1996)
31. M. E. Niyazymbetov, A. L. Laikhter, V. V. Semenov, and D. H. Evans, Tetrahedron Lett., 35, 3037 (1994); K. Tomioka, A. Muraoka, and M. Kanai, J. Org. Chem., 60, 6188 (1995), A. Ito, K. Konishi, and T. Aida, Tetrahedron Lett., 37, 2585 (1996)
32. J. H. Clark, Chem. Rev., 80, 429 (1980).
33. P. G. Sears, R. K. Wolford, and L. R. Dawson, J. Electrochem. Soc., 103, 633 (1956).
34. D. Albanese, D. Landini, and M. Penso, Synthesis, 1994, 34.