Oxidative decarboxylation of α-amino acids: A mild and efficient method for the generation of N-acyliminium ions

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5945-5948

  Boto, Alicia ^a   Hernández, Rosendo ^a   Suárez, Ernesto ^a  

^a CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; N ACYLIMINIUM; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; ISOMERISM; OXIDATION; SYNTHESIS;

EID: 0033529834     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01180-6     Document Type: Article

References (48)

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5. Fontana, F.; Minisci, F.; Barbosa, M. C. N.; Vismara, E. J. Org. Chem. 1991, 56, 2866. Minisci, F.; Vismara, E.; Fontana, F. J. Heterocycl. Chem. 1990, 27, 79. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279. Wilson, C. V. Org. React. 1957, 9, 332. Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219. For some recent examples of oxidative decarboxylation, see: Anger, T.; Graalmann, O.; Schröder, H.; Gerke, R.; Kaiser, U.; Fitjer, L.; Noltemeyer, M. Tetrahedron 1998, 54, 10713. Endo, K.; Hirayama, K.; Aota, Y.; Seya, K.; Asakura, H.; Hisamichi, K. Heterocycles 1998, 47, 865. Paradkar, V. M.; Latham, T. B.; Demko, D. M. Synlett 1995, 1059. Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543.
6. Fontana, F.; Minisci, F.; Barbosa, M. C. N.; Vismara, E. J. Org. Chem. 1991, 56, 2866. Minisci, F.; Vismara, E.; Fontana, F. J. Heterocycl. Chem. 1990, 27, 79. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279. Wilson, C. V. Org. React. 1957, 9, 332. Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219. For some recent examples of oxidative decarboxylation, see: Anger, T.; Graalmann, O.; Schröder, H.; Gerke, R.; Kaiser, U.; Fitjer, L.; Noltemeyer, M. Tetrahedron 1998, 54, 10713. Endo, K.; Hirayama, K.; Aota, Y.; Seya, K.; Asakura, H.; Hisamichi, K. Heterocycles 1998, 47, 865. Paradkar, V. M.; Latham, T. B.; Demko, D. M. Synlett 1995, 1059. Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543.
7. Fontana, F.; Minisci, F.; Barbosa, M. C. N.; Vismara, E. J. Org. Chem. 1991, 56, 2866. Minisci, F.; Vismara, E.; Fontana, F. J. Heterocycl. Chem. 1990, 27, 79. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986. Barton, D. H. R.; Crich, D.; Motherwell, W. B. Tetrahedron 1985, 41, 3901. Sheldon, R. A.; Kochi, J. K. Org. React. 1972, 19, 279. Wilson, C. V. Org. React. 1957, 9, 332. Johnson, R. G.; Ingham, R. K. Chem. Rev. 1956, 56, 219. For some recent examples of oxidative decarboxylation, see: Anger, T.; Graalmann, O.; Schröder, H.; Gerke, R.; Kaiser, U.; Fitjer, L.; Noltemeyer, M. Tetrahedron 1998, 54, 10713. Endo, K.; Hirayama, K.; Aota, Y.; Seya, K.; Asakura, H.; Hisamichi, K. Heterocycles 1998, 47, 865. Paradkar, V. M.; Latham, T. B.; Demko, D. M. Synlett 1995, 1059. Graven, A.; Jorgensen, K. A.; Dahl, S.; Stanczak, A. J. Org. Chem. 1994, 59, 3543.
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19. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
20. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
21. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
22. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
23. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
24. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
25. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
26. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
27. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
28. For recent reviews of iminium and acyliminium chemistry, see: Padwa, A. J. Chem. Soc., Chem. Commun. 1998, 1417. de Koning, H.; Hiemstra, H.; Moolenaar, M. J.; Speckamp, W. N. Eur. J. Org. Chem. 1998, 1729. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. de Koning, H.; Speckamp, W. N. In Methoden der Organischen Chemie, Vol. E21b; (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1995; p 1953. Overman, L. E. Acc. Chem. Res. 1992, 25, 352. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1007. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 271. Hart, D. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 6; Pelletier, S. W. Eds.; Wiley: New York, 1988; p 227. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367. For the generation of iminium ions by decarbonylation of a proline derivative see: Hernández, A. S.; Thaler, A.; Castells, J.; Rapoport, H. J. Org. Chem. 1996, 61, 314.
29. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
30. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
31. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
32. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
33. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
34. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
35. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
36. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
37. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
38. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
39. For some recent applications to synthesis: Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403. Pigeon, P.; Decroix, B. Tetrahedron Lett. 1998, 39, 8659. Wanner, K. T.; Beer, H.; Höfner, G.; Ludwig, M. Eur. J. Org. Chem. 1998, 2019. Kim, J. H.; Lee, Y. S.; Park, H.; Kim, C. S. Tetrahedron 1998, 54, 7395. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144. Nagasaka, T.; Koseki, Y. J. Org. Chem. 1998, 63, 6797. Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914. Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955. Bardot, V.; Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Remuson, R. Heterocycles 1998, 48, 507. Gardette, D.; Gelas-Mialhe, Y.; Gramain, J.-C.; Perrin, B.; Remuson, R. Tetrahedron: Asymmetry 1998, 9, 1823. Wu, X. D.; Khim, S.-K.; Zhang, X.; Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 841.
40. Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Ochiai, M.; Inenaga, M.; Nagao, Y. Tetrahedron Lett. 1988, 29, 6913. Ochiai, M.; Inenaga, M.; Nagao, Y.; Moriarty, R. M.; Vaid, R. K.; Duncan, M. P. Tetrahedron Lett. 1988, 29, 6917.
41. Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Ochiai, M.; Inenaga, M.; Nagao, Y. Tetrahedron Lett. 1988, 29, 6913. Ochiai, M.; Inenaga, M.; Nagao, Y.; Moriarty, R. M.; Vaid, R. K.; Duncan, M. P. Tetrahedron Lett. 1988, 29, 6917.
42. For reviews on Ritter-like reactions: Bishop, R. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; p 261. Addition of acetonitrile to oxycarbenium ions: Kita, Y.; Shibata, N.; Kawano, N.; Yoshida, N.; Matsumoto, K.; Takebe, Y. J. Chem. Soc., Perkin Trans, 1 1996, 2321.
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44. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087. Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, Vol. 1; Wolff, M. E., Ed.; John Wiley & Sons, Inc.: New York, 1995; p 803.
45. Karle, I. L.; Pramanik, A.; Banerjee, A.; Bhattacharjya, S.; Balaram, P. J. Am. Chem. Soc. 1997, 119, 9087. Goodman, M.; Ro, S. In Burger's Medicinal Chemistry and Drug Discovery, Vol. 1; Wolff, M. E., Ed.; John Wiley & Sons, Inc.: New York, 1995; p 803.
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