Regiocontrolled ring opening reactions of a cyclic acetal

Heterocycles

Volumn 52, Issue 2, 2000, Pages 583-586

  Egami, Yuichiro ^a   Takayanagi, Masaru ^a   Tanino, Keiji ^b   Kuwajima, Isao ^c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c KITASATO INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ACETAL; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; ISOMERISM; STEREOCHEMISTRY;

EID: 0034143356     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s105     Document Type: Article

References (23)

1. K. Tanino, T. Shimizu, M. Kuwahara, and I. Kuwajima, J. Org. Chem., 1998, 63, 2422.
2. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
3. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
4. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
5. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
6. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
7. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
8. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
9. Selected examples of use of chiral dioxolane acetals: W. S. Johnson, C. A Harbert, and R. D. Stipanovic, J. Am. Chem. Soc., 1968, 90, 5279; W. J. Richter, J. Org. Chem., 1981, 46, 5119; J. M. McNamara and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7371; H. Sekizaki, M. Jung, J. M. McNamara, and Y. Kishi, J. Am. Chem. Soc., 1982, 104, 7372; P. A. Bartlett, W. S. Johnson, and J. D. Elliot, J. Am. Chem. Soc., 1983, 105, 2088; A. Alexakis, P. Mangeney, A. Ghribi, I. Marek, R. Sedrani, C. Guir, and J. F. Normant, Pure Appl. Chem., 1988, 60, 49; J. F. Normant, A. Alexakis, A. Ghribi, and P. Mangeney, Tetrahedron, 1989, 45, 507; S. G. Davies, R. F. Newton, and J. M. J. Williams, Tetrahedron Lett., 1989, 30, 2967.
10. Studies on the mechanism of reactions of cyclic acetals promoted by Lewis acids: I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and N. G. Almstead, J. Org. Chem., 1989, 56, 6458; S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; T. Sammakia and R. S. Smith, J. Org. Chem., 1992, 57, 2997; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1992, 114, 10998. and references cited there in.
11. Studies on the mechanism of reactions of cyclic acetals promoted by Lewis acids: I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and N. G. Almstead, J. Org. Chem., 1989, 56, 6458; S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; T. Sammakia and R. S. Smith, J. Org. Chem., 1992, 57, 2997; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1992, 114, 10998. and references cited there in.
12. Studies on the mechanism of reactions of cyclic acetals promoted by Lewis acids: I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and N. G. Almstead, J. Org. Chem., 1989, 56, 6458; S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; T. Sammakia and R. S. Smith, J. Org. Chem., 1992, 57, 2997; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1992, 114, 10998. and references cited there in.
13. Studies on the mechanism of reactions of cyclic acetals promoted by Lewis acids: I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and N. G. Almstead, J. Org. Chem., 1989, 56, 6458; S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; T. Sammakia and R. S. Smith, J. Org. Chem., 1992, 57, 2997; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1992, 114, 10998. and references cited there in.
14. Studies on the mechanism of reactions of cyclic acetals promoted by Lewis acids: I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, and C. H. Heathcock, J. Org. Chem., 1990, 55, 6107; S. E. Denmark and N. G. Almstead, J. Org. Chem., 1989, 56, 6458; S. E. Denmark and N. G. Almstead, J. Am. Chem. Soc., 1991, 113, 8089; T. Sammakia and R. S. Smith, J. Org. Chem., 1992, 57, 2997; T. Sammakia and R. S. Smith, J. Am. Chem. Soc., 1992, 114, 10998. and references cited there in.
15. Regiochemistry in hydride reduction of a 4,4-dimethyl-1,3-dioxolane derivative was reported: B. E. Leggetterand R. K. Brown, Can. J. Chem., 1964, 42, 990; B. E. Leggetter and R. K. Brown, Can. J. Chem., 1964, 42, 1005.
16. Regiochemistry in hydride reduction of a 4,4-dimethyl-1,3-dioxolane derivative was reported: B. E. Leggetterand R. K. Brown, Can. J. Chem., 1964, 42, 990; B. E. Leggetter and R. K. Brown, Can. J. Chem., 1964, 42, 1005.
17. A. Hosomi, M. Endo, and H. Sakurai, Chem. Lett., 1976, 941; I. Fleming, J. Dunogues, and R. Smithers, Org. React, 1989, 37, 57; I. Fleming, 'Comprehensive Organic Synthesis,' Vol. 2, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, pp. 563-593.
18. A. Hosomi, M. Endo, and H. Sakurai, Chem. Lett., 1976, 941; I. Fleming, J. Dunogues, and R. Smithers, Org. React, 1989, 37, 57; I. Fleming, 'Comprehensive Organic Synthesis,' Vol. 2, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, pp. 563-593.
19. A. Hosomi, M. Endo, and H. Sakurai, Chem. Lett., 1976, 941; I. Fleming, J. Dunogues, and R. Smithers, Org. React, 1989, 37, 57; I. Fleming, 'Comprehensive Organic Synthesis,' Vol. 2, ed. by B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, pp. 563-593.
20. Presence of an α-chloro ether intermediate was also supposed by Heathcock et al. : see, ref 3.
21. iPr) by method B is not clear at the present stage.
22. Y. Yamamoto, S. Nishii, and J. Yamada, J. Am. Chem. Soc., 1986, 108, 7116; T. Sato, J. Otera, and H. Nozaki, J. Org. Chem., 1990, 55, 6116.
23. Y. Yamamoto, S. Nishii, and J. Yamada, J. Am. Chem. Soc., 1986, 108, 7116; T. Sato, J. Otera, and H. Nozaki, J. Org. Chem., 1990, 55, 6116.