Free bases of chiral N-substituted porphyrins as catalysts for asymmetric reaction

Tetrahedron Letters

Volumn 37, Issue 15, 1996, Pages 2585-2588

  Ito, Akihiko ^a   Konishi, Katsuaki ^a   Aida, Takuzo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029912411     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00376-0     Document Type: Article

References (22)

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2. (b) Swanson, B. A.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1991, 113, 8146.
3. For a recent review, see: Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404.
4. For recent examples of asymmetric syntheses and recognition, see: (a) O'Malley, S.; Kodadek, T. Organometallics 1992, 11, 2299.
5. (b) Mizutani, T; Ema, T.; Tomita, T.; Kuroda, Y.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1993, 520.
6. (c) Konishi, K.; Yahara, K.; Toshishige, H.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1994, 116, 1337.
7. (d) Le Maux, P.; Bahri, H.; Simonneaux. G. J. Chem. Soc., Chem. Commun. 1994, 1287.
8. (a) Kubo, H.; Aida, T.; Inoue, S.; Okamoto, Y. J. Chem. Soc. Chem. Commun. 1998, 1015.
9. (b) Konishi, K.; Sugino, T.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1991, 113, 6487.
10. (c) Konishi, K.; Takahata, Y.; Aida, T.; Inoue, S.; Kuroda, R. J. Am. Chem. Soc. 1993, 115, 1169.
11. Lavallee, D. K. The Chemistry and Biochemistry of N-Substituted Porphyrins; VCH: New York, 1987.
12. (a) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
13. (b) Mukaiyama, T.; Ikegawa, A.; Suzuki, K. Chem. Lett. 1981, 165.
14. 4c
15. Lemiere, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C.; Hiemstra, H.; Wynberg, H.; Jones, J. B.; Toone, E. J. J. Am. Chem. Soc. 1987, 109, 1363.
16. -1) = 423 (-1.1), 401 (9.7), 378 (5.1), 314 (1.0).
17. 3)
18. 1H NMR from the relative signal intensity of pyrrolic N-Me (δ-4.6 - -4.2, 3H) to meso-H (δ 9.5 - 10.2, 4H).
19. No reaction took place with N-acetylbenzylamine alone in the absence of N-substituted porphyrins under similar conditions.
20. 3 with an improved solubility was used in place of 2 for spectroscopic studies. Synthesis of the precursor strapped porphyrin has been reported: Konishi, K.; Oda, K.; Nishida, K.; Aida, T.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 1313.
21. 3295 ([1a]/[3]) = 1.0 (0), 0.84 (0.5), 0.47 (1.0), 0.47 (1.5), 0.48 (2.5).
22. 3c