Enantioselective synthesis of near enantiopure compound by asymmetric autocatalysis triggered by asymmetric photolysis with circularly polarized light

Journal of the American Chemical Society

Volumn 127, Issue 10, 2005, Pages 3274-3275

  Kawasaki, Tsuneomi ^a   Sato, Mirai ^a   Ishiguro, Saori ^a   Saito, Takahiro ^a   Morishita, Yosuke ^a   Sato, Itaru ^a   Nishino, Hideo ^b   Inoue, Yoshihisa ^b   Soai, Kenso ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b Japan Science and Technology Agency   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ORGANIC COMPOUND; PYRIMIDYL ALKANOL; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; CONTROLLED STUDY; ENANTIOSELECTIVITY; IRRADIATION; LIGHT; PHOTODEGRADATION; PHOTOLYSIS; PHOTOSYNTHESIS; RACEMIC MIXTURE;

EID: 14944359662     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0422108     Document Type: Article

References (47)

1. Mislow, K. Collect. Czech. Chem. Commun. 2003, 68, 849-864.
2. (b) Feringa, B. L.; van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418-3438.
3. (c) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2923-2959.
4. (d) Eschenmoser, A. Science 1999, 284, 2118-2124.
5. (e) Zepik, H.; Shavit, E.; Tang, M.; Jensen, T. R.; Kjaer, K.; Bolbach, G.; Leiserowitz, L.; Weissbuch, I.; Lahav, M. Science 2002, 295, 1266-1269.
6. (f) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3139-3154.
7. (g) Kondepudi, D. K.; Asakura, K. Acc. Chem. Res. 2001, 34, 946-954.
8. (h) Siegel, J. S. Chirality 1998, 10, 24-27.
9. (i) Avetisov, V.; Goldanskii, V. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 11435-11442.
10. (j) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios. J. C. Tetrahedron: Asymmetry 2000, 11, 2845-2874.
11. Kuhn, W.; Knopf, E. Z. Phys. Chem. B 1930, 7, 292-310.
12. (b) Bonner, W. A.; Rubenstein, E. BioSystems 1987, 20, 99-111.
13. (c) Nishino, H.; Kosaka, A.; Hembury, G. A.; Aoki, F.; Miyauchi, K.; Shitomi, H.; Onuki, H.; Inoue, Y. J. Am. Chem. Soc. 2002, 124, 11618-11627.
14. Bailey, J.; Chrysostomou, A.; Hough, J. H.; Gledhill, T. M.; McCall, A.; Clark, S.; Menard, F.; Tamura, M. Science 1998, 281, 672-674.
15. Flores, J. J.; Bonner, W. A.; Massey, G. A. J. Am. Chem. Soc. 1977, 99, 3622-3625.
16. (b) Camphor with ca. 20% ee remains after 99% of photodecomposition of racemate: Balavoine, G.; Moradpour, A.; Kagan, H. B. J. Am. Chem. Soc. 1974, 96, 5152-5158.
17. (c) Huck, N. P. M.; Jager, W. F.; de Lang, B.; Feringa, B. L. Science 1996, 273, 1686-1688.
18. (d) Suarez, M.; Schuster, G. B. J. Am. Chem. Soc. 1995, 117, 6732-6738.
19. (e) Kagan, H.; Moradpour, A.; Nicoud, J. F.; Balavoine, G.; Tsoucaris, G. J. Am. Chem. Soc. 1971, 93, 2353-2354.
20. (f) Bernstein, W. J.; Calvin, M.; Buchardt, O. J. Am. Chem. Soc. 1972, 94, 494-498.
21. For reviews, see: (g) Inoue, Y. Chem. Rev. 1992, 92, 741-770. (h) Griesbeck, A. G.; Meierhenrich, U. J. Angew. Chem., Int. Ed. 2002, 41, 3147-3154. (i) Rau, H. In Chiral Photochemistry; Inoue, Y., Ramamaurthy, V., Eds.; Marcel Dekker: New York, 2004; pp 1-44.
22. For reviews, see: (g) Inoue, Y. Chem. Rev. 1992, 92, 741-770. (h) Griesbeck, A. G.; Meierhenrich, U. J. Angew. Chem., Int. Ed. 2002, 41, 3147-3154. (i) Rau, H. In Chiral Photochemistry; Inoue, Y., Ramamaurthy, V., Eds.; Marcel Dekker: New York, 2004; pp 1-44.
23. For reviews, see: (g) Inoue, Y. Chem. Rev. 1992, 92, 741-770. (h) Griesbeck, A. G.; Meierhenrich, U. J. Angew. Chem., Int. Ed. 2002, 41, 3147-3154. (i) Rau, H. In Chiral Photochemistry; Inoue, Y., Ramamaurthy, V., Eds.; Marcel Dekker: New York, 2004; pp 1-44.
24. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
25. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
26. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
27. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
28. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
29. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
30. For reviews, see; (a) Soai, K.; Shibata, T.; Sato, I. Acc. Chem. Res. 2000, 33, 382-390. (b) Soai, K.; Sato, I.; Shibata, T. Chem. Rec. 2001, 1, 321-332. (c) Bolm, C.; Bienewald, F.; Seger, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1657-1659. (d) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C. Chem. Commun. 2000, 887-892. (e) Todd, M. H. Chem. Soc. Rev. 2002, 31, 211-222. (f) Soai, K.; Shibata, T.; Sato, I. Bull. Chem. Soc. Jpn. 2004, 77, 1063-1073. (g) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369-3400.
31. Soai, K.; Shibata, T.; Morioka, H.; Choji, K. Nature 1995, 378, 767-768.
32. (b) Shibata. T.; Yamamoto, J.; Matsumoto, N.; Yonekubo, S.; Osanai, S.; Soai, K. J. Am. Chem. Soc. 1998, 120, 12157-12158.
33. (c) Soai, K.; Osanai, S.; Kadowaki, K.; Yonekubo, S.; Shibata, T.; Sato, I. J. Am. Chem. Soc. 1999, 121, 11235-11236.
34. (d) Sato. I.; Omiya, D.; Saito, T.; Soai, K. J. Am. Chem. Soc. 2000, 122, 11739-11740.
35. (e) Sato, I.; Yamashima, R.; Kadowaki, K.; Yamamoto, J.; Shibata, T.; Soai, K. Angew. Chem., Int. Ed. 2001, 40, 1096-1098.
36. (f) Sato, I.; Kadowaki, K.; Ohgo, Y.; Soai, K. J. Mol. Catal. A: Chem. 2004, 216, 209-214.
37. (g) Sato, I.; Shimizu, M.; Kawasaki, T.; Soai, K. Bull. Chem. Soc. Jpn. 2004, 77, 1587-1588.
38. (h) Kawasaki, T.; Ishikawa, K.; Sekibata, H.; Sato, I.; Soai, K. Tetrahedron Lett. 2004. 45, 7939-7941.
39. (i) Kawasaki, T.; Shimizu, M.; Suzuki, K.; Sato, I.; Soai, K. Tetrahedron: Asymmetry 2004, 15, 3699-3701.
40. (j) Sato, I.; Urabe, H.; Ishiguro, S.; Shibata, T.; Soai, K. Angew. Chem., Int. Ed. 2003, 42, 315-317.
41. (k) Sato, I.; Sugie, R.; Matsueda, Y.; Furumura, Y.; Soai, K. Angew. Chem., Int. Ed. 2004, 43, 4490-4492.
42. Wladimiroff, W. W. Photochem. Photobiol. 1966, 5, 243-250.
43. Inoue, Y.; Ueda, Y.; Hakushi, T. J. Am. Chem. Soc. 1981, 103, 1806-1808.
44. Sato, I.; Yanagi, T.; Soai, K. Chirality 2002, 14, 166-168.
45. We also examined the asymmetric autocatalysis of alkanol 1 initiated by the photoreductive product, 2-alkenylpyrimidyl alkanol, separated from the irradiated mixture under an argon atmosphere. These irradiated olefins gave the opposite enantiomer of 1 to the cryptochiral 1 obtained from the same irradiation mixture, that is, the r-CPL-irradiated cryptochiral (S)-olefin gave (S)-1 with an 88% ee, and the l-CPL-irradiated cryptochiral (R)-olefin induced (R)-1 with a 76% ee. These correlations were reproducible.
46. Mislow, K.; Bickart, P. Isr. J. Chem. 1977, 15, 1-6.
47. The enantiomeric excess values estimated by calculation (refs 2c and 4b,i) of the residual 1 after 10 and 50% asymmetric photolysis of rac-1 are ca. 0.005 and 0.03% ee, respectively (g factor of 1 is ca. 0.001 at 313 nm).