Unprecedented reactions mediated by samarium: An approach to nonstabilized carbonyl ylides

Journal of the American Chemical Society

Volumn 118, Issue 14, 1996, Pages 3533-3534

  Hojo, Makoto ^a   Aihara, Hidenori ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029939039     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954252p     Document Type: Article

References (46)

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31. Intermolecular cross coupling: (a) Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1988, 668-670. (b) Idem J. Org. Chem. 1988, 53, 6077-6084. (c) Kraynack, E. A.; Pedersen, S. F. J. Org. Chem. 1993, 58, 6114-6117. (d) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323. Intramolecular cross coupling: (e) Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
32. Intermolecular cross coupling: (a) Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1988, 668-670. (b) Idem J. Org. Chem. 1988, 53, 6077-6084. (c) Kraynack, E. A.; Pedersen, S. F. J. Org. Chem. 1993, 58, 6114-6117. (d) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323. Intramolecular cross coupling: (e) Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
33. Intermolecular cross coupling: (a) Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1988, 668-670. (b) Idem J. Org. Chem. 1988, 53, 6077-6084. (c) Kraynack, E. A.; Pedersen, S. F. J. Org. Chem. 1993, 58, 6114-6117. (d) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323. Intramolecular cross coupling: (e) Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
34. Intermolecular cross coupling: (a) Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1988, 668-670. (b) Idem J. Org. Chem. 1988, 53, 6077-6084. (c) Kraynack, E. A.; Pedersen, S. F. J. Org. Chem. 1993, 58, 6114-6117. (d) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323. Intramolecular cross coupling: (e) Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
35. Intermolecular cross coupling: (a) Hou, Z.; Takamine, K.; Aoki, O.; Shiraishi, H.; Fujiwara, Y.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1988, 668-670. (b) Idem J. Org. Chem. 1988, 53, 6077-6084. (c) Kraynack, E. A.; Pedersen, S. F. J. Org. Chem. 1993, 58, 6114-6117. (d) Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316-1323. Intramolecular cross coupling: (e) Molander, G. A.; Kenny, C. J. Org. Chem. 1988, 53, 2132-2134. (f) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
36. For a review. see: Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; pp 1-176.
37. 2 After the conventional workup and purification, a pure cycloadduct 5 was obtained.
38. 2 conditions.
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40. From ab initio calculation (STO-3G) for 1,3-dimethylcarbonyl ylide, a sickle coplanar conformation is most stable.
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45. For the 1,3-elimination access to azomethine and thiocarbonyl ylides, see, e.g. (a) Hosomi, A.; Sakata, Y., Sakurai, H. Chem. Lett. 1984 1117-1121. (b) Hosomi, A.; Matsuyama, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1986, 1073-1074.
46. For the 1,3-elimination access to azomethine and thiocarbonyl ylides, see, e.g. (a) Hosomi, A.; Sakata, Y., Sakurai, H. Chem. Lett. 1984 1117-1121. (b) Hosomi, A.; Matsuyama, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1986, 1073-1074.