Reductive Dimerization of Cyclopropane-1,1-dicarboxylic Esters Using Samarium(II) Diiodide (SmI2)

Synlett

Volumn 1996, Issue 6, 1996, Pages 547-548

  Yamashita, Masayuki ^a   Okuyama, Kazunori ^a   Ohhara, Takashi ^a   Kawasaki, Ikuo ^a   Ohta, Shunsaku ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007170785     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5496     Document Type: Article

References (31)

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10. Dimerization using SmI2: a) Girard P.; Couffignal R.; Kagan H. B. Tetrahedron Lett., 22, 3959 (1981). b) Namy J. L.; Kagan H. B. Tetrahedron Lett., 24, 765 (1983). c) Enholm E. J.; Forbes D. C.; Holub D. P. Synth. Commun., 20, 981 (1990). d) Imamoto T.; Nishimura S. Chem. Lett., 1141 (1990). e) Inanaga J.; Handa Y.; Tabuchi T.; Otsubo K.; Yamaguchi M.; Hanamoto T. Tetrahedron Lett., 32, 6557 (1991). f) Liu Y.-S.; Bei M.-Z.; Zhou Z.-H.; Takaki K.; Fujiwara Y. Chem. Lett., 1143 (1992). g) Shiue J.-S.; Lin C.-C.; Fang J.-M. Tetrahedron Lett., 34, 335 (1993).
11. Dimerization using SmI2: a) Girard P.; Couffignal R.; Kagan H. B. Tetrahedron Lett., 22, 3959 (1981). b) Namy J. L.; Kagan H. B. Tetrahedron Lett., 24, 765 (1983). c) Enholm E. J.; Forbes D. C.; Holub D. P. Synth. Commun., 20, 981 (1990). d) Imamoto T.; Nishimura S. Chem. Lett., 1141 (1990). e) Inanaga J.; Handa Y.; Tabuchi T.; Otsubo K.; Yamaguchi M.; Hanamoto T. Tetrahedron Lett., 32, 6557 (1991). f) Liu Y.-S.; Bei M.-Z.; Zhou Z.-H.; Takaki K.; Fujiwara Y. Chem. Lett., 1143 (1992). g) Shiue J.-S.; Lin C.-C.; Fang J.-M. Tetrahedron Lett., 34, 335 (1993).
12. Dimerization using SmI2: a) Girard P.; Couffignal R.; Kagan H. B. Tetrahedron Lett., 22, 3959 (1981). b) Namy J. L.; Kagan H. B. Tetrahedron Lett., 24, 765 (1983). c) Enholm E. J.; Forbes D. C.; Holub D. P. Synth. Commun., 20, 981 (1990). d) Imamoto T.; Nishimura S. Chem. Lett., 1141 (1990). e) Inanaga J.; Handa Y.; Tabuchi T.; Otsubo K.; Yamaguchi M.; Hanamoto T. Tetrahedron Lett., 32, 6557 (1991). f) Liu Y.-S.; Bei M.-Z.; Zhou Z.-H.; Takaki K.; Fujiwara Y. Chem. Lett., 1143 (1992). g) Shiue J.-S.; Lin C.-C.; Fang J.-M. Tetrahedron Lett., 34, 335 (1993).
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28. 2-THF-HMPA system in the presence of proton sources but in the absence of HMPA almost no reaction or slow reduction of the double bond took place.
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30. 1H-NMR, IR, MS, and high-resolution MS) for the compounds (2a - 2f) were obtained.
31. 4, and evaporated. The residue was chromatographed on preparative TLC (silica gel; AcOEt/hexane) to give the diastereomeric mixture of 2.