Iron-catalyzed regio- and stereoselective ring opening of [2.2.1]-and [3.2.1]oxabicyclic alkenes with a Grignard reagent

Organic Letters

Volumn 5, Issue 8, 2003, Pages 1373-1375

  Nakamura, Masaharu ^a,b   Matsuo, Keiko ^b   Inoue, Toshihiro ^b   Nakamura, Eiichi ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; IRON;

ARTICLE; CATALYSIS; GRIGNARD REACTION; RING OPENING; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0141740671     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034375b     Document Type: Article

References (25)

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3. A number of examples of iron-catalyzed coupling reactions have been reported as efficient C-C bond formation reactions. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360. (c) Takacs, M. J.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. (d) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514. (e) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017-6028. (f) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700-1701. (g) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205. (h) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901-1903. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 and references therein.
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6. A number of examples of iron-catalyzed coupling reactions have been reported as efficient C-C bond formation reactions. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360. (c) Takacs, M. J.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. (d) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514. (e) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017-6028. (f) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700-1701. (g) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205. (h) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901-1903. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 and references therein.
7. A number of examples of iron-catalyzed coupling reactions have been reported as efficient C-C bond formation reactions. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360. (c) Takacs, M. J.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. (d) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514. (e) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017-6028. (f) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700-1701. (g) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205. (h) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901-1903. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 and references therein.
8. A number of examples of iron-catalyzed coupling reactions have been reported as efficient C-C bond formation reactions. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360. (c) Takacs, M. J.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. (d) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514. (e) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017-6028. (f) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700-1701. (g) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205. (h) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901-1903. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 and references therein.
9. A number of examples of iron-catalyzed coupling reactions have been reported as efficient C-C bond formation reactions. (a) Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487-1489. (b) Kochi, J. K. Acc. Chem. Res. 1974, 7, 351-360. (c) Takacs, M. J.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. (d) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett 1991, 513-514. (e) Yanagisawa, A.; Nomura, N.; Yamamoto, H. Tetrahedron 1994, 50, 6017-6028. (f) Reddy, C. K.; Knochel, P. Angew. Chem., Int. Ed. 1996, 35, 1700-1701. (g) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199-1205. (h) Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901-1903. (k) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863 and references therein.
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