Facile α-deprotunation-electrophilic substitution of quinuclidine and DABCO

Chemical Communications

Volumn , Issue 19, 1999, Pages 1927-1928

  Kessar, Satinder V ^a   Singh, Paramjit ^a   Singh, Kamal N ^a   Singh, Sandeep K ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; PROTON; QUINUCLIDINE;

ARTICLE; CHEMICAL REACTION; ELECTROPHILE; SYNTHESIS;

EID: 0033533879     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905359j     Document Type: Article

References (21)

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2. R. Verpoorte, J. Shripsema and T. van der Leer, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1988, vol. 34, p 332; M. S. Ashwood, A. W. Gibson, P. G. Houghton, G. R. Humphrey, D. C. Roberts and S. H. B. Wright, J. Chem. Soc., Perkin. Trans. 1, 1995, 641; K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768; K. E. Simons, A. Ibbotson, P. Johnston, H. Plum and P. B. Wells, J. Catal., 1994, 150, 321; M. J. O'Donnell, Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 389.
3. R. Verpoorte, J. Shripsema and T. van der Leer, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1988, vol. 34, p 332; M. S. Ashwood, A. W. Gibson, P. G. Houghton, G. R. Humphrey, D. C. Roberts and S. H. B. Wright, J. Chem. Soc., Perkin. Trans. 1, 1995, 641; K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768; K. E. Simons, A. Ibbotson, P. Johnston, H. Plum and P. B. Wells, J. Catal., 1994, 150, 321; M. J. O'Donnell, Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 389.
4. R. Verpoorte, J. Shripsema and T. van der Leer, The Alkaloids, ed. A. Brossi, Academic Press, New York, 1988, vol. 34, p 332; M. S. Ashwood, A. W. Gibson, P. G. Houghton, G. R. Humphrey, D. C. Roberts and S. H. B. Wright, J. Chem. Soc., Perkin. Trans. 1, 1995, 641; K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768; K. E. Simons, A. Ibbotson, P. Johnston, H. Plum and P. B. Wells, J. Catal., 1994, 150, 321; M. J. O'Donnell, Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 389.
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14. 3 activation is ineffective in this case although it is very useful for removal of more acidic α-protons. M. R. Ebden, N. S. Simpkins and D. N. A. Fox, Tetrahedron Lett., 1995, 36, 8697; E. Vedejs and J. T. Kendall, J. Am. Chem. Soc., 1997, 119, 6941.
15. 3 activation is ineffective in this case although it is very useful for removal of more acidic α-protons. M. R. Ebden, N. S. Simpkins and D. N. A. Fox, Tetrahedron Lett., 1995, 36, 8697; E. Vedejs and J. T. Kendall, J. Am. Chem. Soc., 1997, 119, 6941.
16. 3 reduction modification of this procedure see: K. B. Sharpless, H. C. Kolb and P. G. Andersson, J. Am. Chem. Soc., 1994, 116, 1278.
17. 3 reduction modification of this procedure see: K. B. Sharpless, H. C. Kolb and P. G. Andersson, J. Am. Chem. Soc., 1994, 116, 1278.
18. The threo and erythro configurations were assigned on the basis of coupling constants between C-2 and C-9 methine protons in the NMR spectrum. T. Kametani, H. Matsumoto, Y. Satoh, H. Nemoto and K. Fukumoto, J. Chem. Soc., Perkin Tram. 1, 1977, 376.
19. T. Cohen, W. M. Daniewski and R. B. Weisenfeld, Tetrahedron Lett., 1978, 4665.
20. K. B. Sharpless and R. Oi, Tetrahedron Lett., 1991, 32, 4853.
21. K. Soai, A. Oshio and H. Yoneyama, Tetrahedron: Asymmetry, 1992, 3, 359.