Lewis acid mediated [2,3]-sigmatropic rearrangement of allylic ammonium ylides

Tetrahedron Letters

Volumn 44, Issue 15, 2003, Pages 3159-3162

  Blid, Jan ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Ammonium ylide; Lewis acid; 2,3 sigmatropic rearrangement

Indexed keywords

ALLYL COMPOUND; AMINE; AMMONIUM DERIVATIVE; BASE; BORON; LEWIS ACID; PHOSPHORUS DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; STEREOCHEMISTRY;

EID: 0037424786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00510-0     Document Type: Article

References (28)

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5. For instance: (a) Doyle, M. P.; Griffin, J. H.; Chinn, M. S.; van Leusen, D. J. Org. Chem. 1984, 49, 1917-1925; (b) Pirrung, M. C.; Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060-6062; (c) Roskamp, E. J.; Johnson, C. R. J. Am. Chem. Soc. 1986, 108, 6062-6063.
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12. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
13. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
14. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
15. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
16. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
17. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
18. Selected references: (a) Vedejs, E.; Arco, M. J.; Powell, D. W.; Renga, J. M.; Singer, S. P. J. Org. Chem. 1978, 43, 4831-4837; (b) Mander, L. N.; Turner, J. V. Aust. J. Chem. 1980, 33, 1559-1568; (c) Jemison, R. W.; Laird, T.; Ollis, W. D.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1980, 1450-1457; (d) Honda, K.; Igarashi, D.; Asami, M.; Inoue, S. Synlett 1998, 685-687; (e) Glaeske, K. W.; West, F. G. Org. Lett. 1999, 1, 31-33; (f) Arboré, A. P. A.; Cane-Honeysett, D. J.; Coldham, I.; Middleton, M. L. Synlett 2000, 236-238; (g) Sweeney, J. B.; Tavassoli, A.; Carter, N. B.; Hayes, J. F. Tetrahedron 2002, 58, 10113-10126.
19. To our knowledge only three prior attempts have been made with Lewis acid mediated [2,3]-sigmatropic rearrangements of allylic amines: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072; (b) Kessar, S. V.; Singh, P.; Kaul, V. K.; Kumar, G. Tetrahedron Lett. 1995, 36, 8481-8484; (c) Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1998, 2817-2821.
20. To our knowledge only three prior attempts have been made with Lewis acid mediated [2,3]-sigmatropic rearrangements of allylic amines: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072; (b) Kessar, S. V.; Singh, P.; Kaul, V. K.; Kumar, G. Tetrahedron Lett. 1995, 36, 8481-8484; (c) Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1998, 2817-2821.
21. To our knowledge only three prior attempts have been made with Lewis acid mediated [2,3]-sigmatropic rearrangements of allylic amines: (a) Murata, Y.; Nakai, K. Chem. Lett. 1990, 2069-2072; (b) Kessar, S. V.; Singh, P.; Kaul, V. K.; Kumar, G. Tetrahedron Lett. 1995, 36, 8481-8484; (c) Coldham, I.; Middleton, M. L.; Taylor, P. L. J. Chem. Soc., Perkin Trans. 1 1998, 2817-2821.
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24. 13C NMR, IR and HRMS).
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26. Ishihara K. Yamamoto H. Lewis Acids in Organic Synthesis. 1:2000;89-133 Wiley-VCH, Weinheim.
27. C 172.8, 140.7, 140.3, 128.2, 128.2, 126.8, 114.7, 63.1, 52.1, 46.2, 45.5, 41.4, 26.0, 24.2, 15.9.
28. 2+-cyclization to the corresponding pyrrolidines followed by NOE interactions measurements.