Stereoselective dimerization of α-keto amides using samarium diiodide

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7755-7756

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

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; TARTARIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030597042     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01769-8     Document Type: Article

References (18)

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4. 2. For reviews : Kagan, H, B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Inanaga, J. J. Synth. Org. Chem., Jpn. 1989, 47, 200-211. Kagan, H. B. New J. Chem. 1990, 14, 453-460. Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23. Molander, G. A. Chem. Rew. 1992, 92, 29-68.
5. 2. For reviews : Kagan, H, B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Inanaga, J. J. Synth. Org. Chem., Jpn. 1989, 47, 200-211. Kagan, H. B. New J. Chem. 1990, 14, 453-460. Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23. Molander, G. A. Chem. Rew. 1992, 92, 29-68.
6. 2. For reviews : Kagan, H, B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Inanaga, J. J. Synth. Org. Chem., Jpn. 1989, 47, 200-211. Kagan, H. B. New J. Chem. 1990, 14, 453-460. Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23. Molander, G. A. Chem. Rew. 1992, 92, 29-68.
7. 2. For reviews : Kagan, H, B.; Namy, J. L. Tetrahedron, 1986, 42, 6573-6614. Inanaga, J. J. Synth. Org. Chem., Jpn. 1989, 47, 200-211. Kagan, H. B. New J. Chem. 1990, 14, 453-460. Soderquist, J. A. Aldrichimica Acta, 1991, 24, 15-23. Molander, G. A. Chem. Rew. 1992, 92, 29-68.
8. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
9. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
10. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
11. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
12. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
13. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
14. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
15. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
16. 3. Erlenmeyer, E. Ber. 1905, 38, 3119-3125. Schönberg, A.; Latif, N.; Moubasher, R.; Sina, A. J. Chem. Soc. 1951, 1364-1368. Juday, R. E. J. Org. Chem. 1958, 23, 1010-1012. Barker, S. A.; Brimacombe, J. S.; Spence, D. H. J. Chem. Soc. 1963, 5117-5122. Leermakers, P. A.; Vesley, G. F. J. Am. Chem. Soc. 1963, 85, 3776-3779. Katsaros, N.; Vrachnou-Astra, E.; Konstantatos, J.; Stassinopoulou, C. I. Tetrahedron Lett. 1979, 4319-4322. Negron-Mendoza, A.; Albarran, G. Radiat. Phys. Chem. 1990, 35, 469-472. Abe, K.; Takahashi, S.; Mori, N. Chem. Express, 1991, 6, 53-56. Markova, E, A.; Kolomiets, A. F.; Fokin, A. V. Izu. Akad. Nauk, Ser. Khim. 1992, 1408-1411.
17. -1, F(000) = 4860, T = 296 K, R = 0.050 for 2009 observations. Detailed X-ray crystallographic data of 2ra, 2ma, 2re, 2rh, and 2ri are available from the Cambridge Crystallographic Data Centre.
18. 1H-NMR, IR, LRMS, and HRMS or elemental analysis.