Chelation control through the coordination of Lewis acids to an acetylenic π-bond

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4817-4818

  Asao, Naoki ^a   Asano, Toru ^a   Ohishi, Takeshi ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALDEHYDE; ALKYNE; CYCLOHEXANE DERIVATIVE;

ARTICLE; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0034679098     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994000e     Document Type: Article

References (28)

1. For reviews, see: (a) Yamamoto, H. Lewis Acid Chemistry: A Practical Approach: Oxford University Press: Oxford, 1999. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120. (c) Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis: CRC Press: Boca Raton, 1996. (d) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 283- 324.
2. For reviews, see: (a) Yamamoto, H. Lewis Acid Chemistry: A Practical Approach: Oxford University Press: Oxford, 1999. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120. (c) Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis: CRC Press: Boca Raton, 1996. (d) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 283- 324.
3. For reviews, see: (a) Yamamoto, H. Lewis Acid Chemistry: A Practical Approach: Oxford University Press: Oxford, 1999. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120. (c) Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis: CRC Press: Boca Raton, 1996. (d) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 283- 324.
4. For reviews, see: (a) Yamamoto, H. Lewis Acid Chemistry: A Practical Approach: Oxford University Press: Oxford, 1999. (b) Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120. (c) Santelli, M.; Pons, J. M. Lewis Acids and Selectivity in Organic Synthesis: CRC Press: Boca Raton, 1996. (d) Shambayati, S.; Schreiber, S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 283-324.
5. The Lewis basicity of the lone pair of imine's nitrogen and aldehyde's oxygen atom is, in general, stronger than that of the π-electron of C-C double and triple bonds. Accordingly it is reasonable that all the previous examples for the synthetically useful chelation controlled reactions are concerning the coordination to lone pair electrons. The interaction of alkynes with Lewis acids was studied by NMR and IR spectroscopy, see: (a) Hogeveen, H.; Kok, D. M. Tetrahedron Lett. 1980, 21, 659-662. (b) Perkampus, H. H.; Weiss, W. Z. Naturforsch. 1974, 29b, 61-64.
6. The Lewis basicity of the lone pair of imine's nitrogen and aldehyde's oxygen atom is, in general, stronger than that of the π-electron of C-C double and triple bonds. Accordingly it is reasonable that all the previous examples for the synthetically useful chelation controlled reactions are concerning the coordination to lone pair electrons. The interaction of alkynes with Lewis acids was studied by NMR and IR spectroscopy, see: (a) Hogeveen, H.; Kok, D. M. Tetrahedron Lett. 1980, 21, 659-662. (b) Perkampus, H. H.; Weiss, W. Z. Naturforsch. 1974, 29b, 61-64.
7. 3SnH (0.2 and 0.4 equiv) was carried out. The ratios of 4a/5a, determined both by NMR and by GC analysis, were essentially identical with those shown in entry 1.
8. 2-promoted reduction of a 1:1 mixture of 1a and 3a gave a 62:38 mixture of 4a and 5a in 52% combined yield.
9. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
10. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
11. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373-2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
12. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic-Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
13. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
14. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832- 4841.
15. Several examples of aluminum pentacoordinate complexes have been isolated and characterized, see: (a) Heitsch, C. W.; Nordman, C. E.; Parry, P. W. Inorg. Chem. 1963, 2, 508. (b) Palenick, G. Acta Crystallogr. 1964, 17, 1573-1580. (c) Beattie, I. R.; Ozin, G. A. J. Chem. Soc. A 1968, 2373- 2377. (d) von Vliet, M. R. P.; Buysingh, P.; von Koten, G.; Vrieze, K.; Kojic- Prodic, B.; Spek, A. L. Organometallics 1985, 4, 1701-1707. (e) Bennett, F. R.; Elms, F. M.; Gardiner, M. G.; Koutsantonis, G. A.; Raston, C. L.; Roberts, N. K. Organometallics 1992, 11, 1457-1459. (f) Muller, G.; Lachmann, J.; Rufinska, A. Organometallics 1992, 11, 2970-2972. (g) Fryzuk, M. D.; Giesbrecht, G. R.; Olovsson, G.; Rettig, S. J. Organometallics 1996, 15, 4832-4841.
16. Aluminum and gallium Lewis acids are known to act as bidntate Lewis acids. For aluminum Lewis acid, see: (a) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829-833. (b) Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem Soc. 1999, 121, 3328-3333. (c) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457-4460. (d) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256. For gallium Lewis acid, see: (e) Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5881-5884.
17. Aluminum and gallium Lewis acids are known to act as bidntate Lewis acids. For aluminum Lewis acid, see: (a) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829-833. (b) Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem Soc. 1999, 121, 3328-3333. (c) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457-4460. (d) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256. For gallium Lewis acid, see: (e) Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5881-5884.
18. Aluminum and gallium Lewis acids are known to act as bidntate Lewis acids. For aluminum Lewis acid, see: (a) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829-833. (b) Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem Soc. 1999, 121, 3328-3333. (c) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457-4460. (d) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256. For gallium Lewis acid, see: (e) Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5881-5884.
19. Aluminum and gallium Lewis acids are known to act as bidntate Lewis acids. For aluminum Lewis acid, see: (a) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829-833. (b) Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem Soc. 1999, 121, 3328-3333. (c) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457-4460. (d) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256. For gallium Lewis acid, see: (e) Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5881-5884.
20. Aluminum and gallium Lewis acids are known to act as bidntate Lewis acids. For aluminum Lewis acid, see: (a) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829-833. (b) Ooi, T.; Kagoshima, N.; Ichikawa, H.; Maruoka, K. J. Am. Chem Soc. 1999, 121, 3328-3333. (c) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457-4460. (d) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256. For gallium Lewis acid, see: (e) Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5881-5884.
21. The hypercoodinated aluminum Lewis acids have been used for asymmetric reactions; see: (a) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551-10552. (b) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (c) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442.
22. The hypercoodinated aluminum Lewis acids have been used for asymmetric reactions; see: (a) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551-10552. (b) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (c) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442.
23. The hypercoodinated aluminum Lewis acids have been used for asymmetric reactions; see: (a) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551-10552. (b) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713-11714. (c) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441-442.
24. 3-mediated carbogallation of alkynes was reported, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074-4075. (b) Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743-744. (c) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313-1315. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1995, 1093-1094.
25. 3-mediated carbogallation of alkynes was reported, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074-4075. (b) Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743-744. (c) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313-1315. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1995, 1093-1094.
26. 3-mediated carbogallation of alkynes was reported, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074-4075. (b) Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743-744. (c) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313-1315. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1995, 1093-1094.
27. 3-mediated carbogallation of alkynes was reported, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074-4075. (b) Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743-744. (c) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313-1315. (d) Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1995, 1093-1094.
28. One referee mentioned the rate difference between 1a and 2: it is only 4:1, while the difference between 1a and 3a is 32:1. The following results clearly indicate that the presence of an electron-donating group at the ortho position facilitates the reduction. Accordingly, the rate difference of 1a/2 is lower than that of 1a/3a. (formula presented)