Acid-catalyzed Grob fragmentation reactions of acetonides derived from terpenes

Organic Letters

Volumn 5, Issue 6, 2003, Pages 905-908

  Barluenga, José ^a   Álvarez Pérez, Mónica ^a   Wuerth, Kirsten ^a   Rodríguez, Félix ^a   Fañanás, Francisco J ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONIDE; ACID; ALDEHYDE; BORON TRIFLUORIDE; CHEMICAL COMPOUND; CYCLOBUTANE; CYCLOPROPANE; TERPENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DERIVATIZATION; FRAGMENTATION REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0141516238     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034083a     Document Type: Article

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29. 2 to favor Grob fragmentations can also be found in previous works. (a) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. Chem. Commun. 1990, 1538-1539. (b) Yamamoto, T.; Suemune, H.; Sakai, K. Tetrahedron 1991, 47, 8523-8528. (c) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron Lett. 1998, 39, 8071-8072. (d) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1998, 63, 6438-6439. (e) Kabalka, G. W.; Li, N.-S.; Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, 3157-3161. See also refs 2c and 4e.
30. 2 to favor Grob fragmentations can also be found in previous works. (a) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. Chem. Commun. 1990, 1538-1539. (b) Yamamoto, T.; Suemune, H.; Sakai, K. Tetrahedron 1991, 47, 8523-8528. (c) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron Lett. 1998, 39, 8071-8072. (d) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1998, 63, 6438-6439. (e) Kabalka, G. W.; Li, N.-S.; Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, 3157-3161. See also refs 2c and 4e.
31. 2 to favor Grob fragmentations can also be found in previous works. (a) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. Chem. Commun. 1990, 1538-1539. (b) Yamamoto, T.; Suemune, H.; Sakai, K. Tetrahedron 1991, 47, 8523-8528. (c) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron Lett. 1998, 39, 8071-8072. (d) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1998, 63, 6438-6439. (e) Kabalka, G. W.; Li, N.-S.; Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, 3157-3161. See also refs 2c and 4e.
32. 2 to favor Grob fragmentations can also be found in previous works. (a) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. Chem. Commun. 1990, 1538-1539. (b) Yamamoto, T.; Suemune, H.; Sakai, K. Tetrahedron 1991, 47, 8523-8528. (c) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron Lett. 1998, 39, 8071-8072. (d) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1998, 63, 6438-6439. (e) Kabalka, G. W.; Li, N.-S.; Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, 3157-3161. See also refs 2c and 4e.
33. 2 to favor Grob fragmentations can also be found in previous works. (a) Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K. Chem. Commun. 1990, 1538-1539. (b) Yamamoto, T.; Suemune, H.; Sakai, K. Tetrahedron 1991, 47, 8523-8528. (c) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. Tetrahedron Lett. 1998, 39, 8071-8072. (d) Kabalka, G. W.; Tejedor, D.; Li, N.-S.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1998, 63, 6438-6439. (e) Kabalka, G. W.; Li, N.-S.; Tejedor, D.; Malladi, R. R.; Trotman, S. J. Org. Chem. 1999, 64, 3157-3161. See also refs 2c and 4e.
34. De Giacomo, M.; Bettolo, R. M.; Scarpelli, R. Tetrahedron Lett. 1997, 38, 3469-3470. See also refs 10b-e.
35. To read about recent calculations on cations in Grob fragmentations, see: Alder, R. W.; Harvey, J. N.; Oakley, M. T. J. Am. Chem. Soc. 2002, 124, 4960-4961.