Application of the silicon-tether strategy for controlling the regioselectivity and diastereoselectivity of intramolecular nitrone cycloadditions for aminopolyol synthesis

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7633-7637

  Ishikawa, Teruhiko ^a   Kudo, Takayuki ^a   Shigemori, Kazunori ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NITRONE DERIVATIVE; POLYOL; SILICON;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034674969     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000248o     Document Type: Article

References (44)

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17. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
18. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
19. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421-3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
20. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
21. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
22. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668-1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
23. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
24. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
25. To the best of our knowledge, this is the first example of generalized silicon-tether strategy for an intramolecular nitrone-olefin cycloaddition reaction. For only one fragmentary example of the reaction of this class, see: (a) Rong, J.; Roselt, P.; Plavec, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 4921 -4936. For intermolecular nitrone-vinylsilane cycloaddition reactions, see: (b) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189-3195. (c) DeShong, P.; Leginus, J. M. J. Org. Chem. 1984, 49, 3421- 3423. (d) DeShong, P.; Leginus, J. M.; Lander, S. W., Jr. J. Org. Chem. 1986, 51, 574-576. For the silicon-tether strategy for intramolecular [3 + 2] cycloaddition reactions other than nitrones, see: (e) Righi, P.; Marotta, E.; Landuzzi, A.; Rosini, G. J. Am. Chem. Soc. 1996, 118, 9446-9447. (f) Denmark, S. E.; Hurd, A. R.; Sacha, H. J. J. Org. Chem. 1997, 62, 1668- 1674. (g) Garner, P.; Cox, P. B.; Anderson, J. T.; Protasiewicz, J.; Zaniewski, R. J. Org. Chem. 1997, 62, 493-498. (h) Young, D. G. J.; G.-Bengoa, E.; Hoveyda, A. H. J. Org. Chem. 1999, 64, 692-693. (i) Marrugo, H.; Dogbéavou, R.; Breau, L. Tetrahedron Lett. 1999, 40, 8979-8983.
26. For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry: Larson, G. L., Ed.; Vol. 3, Jai Press: 1996; pp 1-62. (b) Fleming, I. Chemtracts, Org. Chem. 1996, 9, 1-64. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662. See also: (d) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
27. For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry: Larson, G. L., Ed.; Vol. 3, Jai Press: 1996; pp 1-62. (b) Fleming, I. Chemtracts, Org. Chem. 1996, 9, 1-64. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662. See also: (d) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
28. For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry: Larson, G. L., Ed.; Vol. 3, Jai Press: 1996; pp 1-62. (b) Fleming, I. Chemtracts, Org. Chem. 1996, 9, 1-64. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662. See also: (d) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
29. For reviews, see: (a) Tamao, K. In Advances in Silicon Chemistry: Larson, G. L., Ed.; Vol. 3, Jai Press: 1996; pp 1-62. (b) Fleming, I. Chemtracts, Org. Chem. 1996, 9, 1-64. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662. See also: (d) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organometallics 1983, 2, 1694-1696.
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38. Eliel, E. L.; Wilen, S. H.; Mander L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 695-698.
39. 2=CH- group is 1.68 kcal/mol.
40. H: see Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction: Evidence, Nature, and Consequences; Wiley-VCH: New York, 1998.
41. Cycloadducts with the regiochemistry of 4 may be obtained in the intermolecular cycloaddition if substituted vinylsilanes such as β-trimethylsilylstyrene is used as a dipolarophile: see ref 9d.
42. This ratio was conveniently determined by the signal intensity of the methyl carbons on the stereocenter (see Supporting Information).
43. LeBel discussed the possibility of nitrone syn-anti interconversion when a solution of the nitrone in EtOH or toluene was heated at reflux, see: LeBel, N. A.; Banucci, E. G. J. Org. Chem. 1971, 36, 2440-2448.
44. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 837-838.