Generation and cycloaddition of polymer-supported azomethine ylide by utilizing the characteristics of silicon: A facile route to pyrrolidines and pyrroles from α-silylimines bound to resin

Tetrahedron

Volumn 59, Issue 2, 2003, Pages 197-205

  Okada, Hirofumi ^a   Akaki, Tatsuo ^a   Oderaotoshi, Yoji ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,2 silatropy; 1,3 dipolar cycloaddition; Azomethine ylide; Pyrrole; Pyrrolidine; Solid phase synthesis

Indexed keywords

ALPHA SILYLIMINE; AZOMETHINE YLIDE; IMINE; NITROGEN; POLYMER; PYRROLE DERIVATIVE; PYRROLIDINE DERIVATIVE; RESIN; SILANE DERIVATIVE; SILICON; TRIFLUOROSILANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLOADDITION; DESILYLATION; PRIORITY JOURNAL; SOLID;

EID: 0037421133     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01473-4     Document Type: Article

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13. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
14. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
15. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
16. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
17. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
18. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
19. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
20. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
21. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
22. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
23. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
24. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
25. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
26. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
27. For recent examples, see: (b) Cheng W.-C., Wong M., Olmstead M.M., Kurth M.J. Org. Lett. 4:2002;741-744 (c) Shang Y.-J., Wang Y.-G. Tetrahedron Lett. 43:2002;2247-2249 (d) Faita G., Mella M., Mortoni A., Paio A., Quadrelli P., Seneci P. Eur. J. Org. Chem. 2002;1175-1183 (e) Barrett A.G.M., Boffey R.J., Frederiksen M.U., Newton C.G., Roberts R.S. Tetrahedron Lett. 42:2001;5579-5581 (f) Hoveyda H.R., Hall D.G. Org. Lett. 3:2001;3491-3494 (g) Faita G., Paio A., Quadrelli P., Rancati F., Seneci P. Tetrahedron Lett. 41:2000;1265-1269 (h) Dondas H.A., Grigg R., MacLachlan W.S., MacPherson D.T., Markandu J., Sridharan V., Suganthan S. Tetrahedron Lett. 41:2000;967-970 (i) Park K.-H., Kurth M.J. Tetrahedron Lett. 40:1999;5841-5844 (j) Gong Y.-D., Najdi S., Olmstead M.M., Kurth M.J. J. Org. Chem. 63:1998;3081-3086 (k) Bilodeau M.T., Cunningham A.M. J. Org. Chem. 63:1998;2800-2801 (l) Kobayashi S., Akiyama R. Tetrahedron Lett. 39:1998;9211-9214 (m) Whitehouse D.L., Nelson K.H., Savinov S.N., Löwe R.S., Austin D.J. Bioorg. Med. Chem. 6:1998;1273-1282 (n) Whitehouse D.L., Nelson K.H. Jr, Savinov S.N., Austin D.J. Tetrahedron Lett. 38:1997;7139-7142 (o) Gowravaram M.R., Gallop M.A. Tetrahedron Lett. 38:1997;6973-6976 (p) Kurth M.J., Randall L.A.A., Takenouchi K. J. Org. Chem. 61:1996;8755-8761 (q) Murphy M.M., Schullek J.R., Gordon E.M., Gallop M.A. J. Am. Chem. Soc. 117:1995;7029-7030 (r) Beebe X., Chiappari C.L., Olmstead M.M., Kurth M.J., Schore N.E. J. Org. Chem. 60:1995;4204-4212.
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