Highly efficient asymmetric paternò-büchi reaction in a microcapillary reactor utilizing slug flow

Journal of Flow Chemistry

Volumn 4, Issue 1, 2014, Pages 35-39

  Terao, Kimitada ^a   Nishiyama, Yasuhiro ^a   Kakiuchi, Kiyomi ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

asymmetric reaction; flow reactor; Patern B chi photoreaction; photochemistry; slug flow mode

Indexed keywords

EID: 84896332439     PISSN: 2062249X     EISSN: 20630212     Source Type: Journal    
DOI: 10.1556/JFC-D-13-00035     Document Type: Article

References (42)

1. (a) Ciana, C.-L.; Bochet C. G. Chimia 2007, 61, 650
2. (b) Oelgemöller, M.; Healy, N.; de Oliveira, L.; Jung, C.; Mattay J. Green Chem. 2006, 8, 831
3. (c) Hoffmann, N. Chem. Rev. 2008, 108, 1052
4. (d) Bach, T.; Hehn, J. P. Angew. Chem. Int. Ed. 2011, 50, 1000.
5. (a) Yoshida, J. Flash Chemistry: Fast Organic Synthesis in Microsystems; Wiley: Hoboken, 2008
6. (b) Fukuyama, T.; Rahman, M. T.; Sato, M.; Ryu, I.; Synlett 2008, 151
7. (c) Yoshida, J.; Nagaki, A.; Yamada, T. Chem.-Eur. J. 2008, 14, 7450
8. (d) McMullen, J. P.; Jensen, K. F. Annu. Rev. Anal. Chem. 2010, 3, 19
9. (e) Razzaq, T.; Kappe, C. O. Chem.-Asian J. 2010, 5, 1274
10. (f) Suga, S.; Yamada, D.; Yoshida, J. Chem. Lett. 2010, 39, 404
11. (g) Yoshida, J.; Kim, H.; Nagaki, A. Chem Sus Chem 2011, 4, 331
12. (h) Pastre, J. C.; Browne, D. L.; Ley, S. V. Chem. Soc. Rev. 2013, 42, 8849.
13. (a) Matsushita, Y.; Ichimura, T.; Ohba, N.; Kumada, S.; Sakeda, K. Suzuki, T.; Tanibata, H.; Murata, T. Pure Appl. Chem. 2007, 79, 1959
14. (b) Knowles. J. P.; Elliott, L. D.; Booker-Milburn, K. I. Beilstein J. Org. Chem. 2012, 8, 2025
15. (c) Shvydkiv, O.; Oelgemöller, M. CRC handbook of Organic Photochemistry and Photobiology; Griesbeck, A.; Oelgemöller, M.; Ghetti, F., Ed.; CRC Press: Boca Raton, 2012, pp. 49-72
16. (d) Noël, T.; Wang, X.; Hessel, V. Chimia Oggi 2013, 31, 10.
17. (a) Asano, K.; Uesugi, Y.; Yoshida, J. Org. Lett. 2013, 15, 2398
18. (b) Lumley, E. K.; Dyer, C. E.; Pamme, N.; Boyle, R. W. Org. Lett. 2012, 14, 5724
19. (c) Fukuyama, T.; Kajihara, Y.; Hino, Y.; Ryu, I. J. Flow Chem. 2011, 1, 40
20. (d) Fuse, S.; Mifune, Y.; Tanabe, N.; Takahashi, T. Org. Biomol. Chem. 2012, 10, 5205
21. (e) Kopetzki, D.; Levesque, F.; Seeberger, P. H. Chem.-Eur. J. 2013, 19, 5450.
22. (a) Mukae, H.; Maeda, H.; Nashihara, S.; Mizuno, K. Bull. Chem. Soc. Jpn. 2007, 80, 1157
23. (b) Horie, T.; Sumino, M.; Tanaka, T.; Matsushita, Y.; Ichimura, T.; Yoshida, J. Org. Proc. Res. Dev. 2010, 14, 405
24. (c) Yavorskyy, A.; Shvydkiv, O.; Hoffmann, N.; Nolan, K.; Oelgemöller, M. Org. Lett. 2012, 14, 4342
25. (d) Maskill, K. G.; Knowles, J. P.; Elliott, L. D.; Alder, R. W.; Booker-Milburn, K. I. Angew. Chem. Int. Ed. 2013, 52, 1499
26. (e) Claudius-Brandt, S.; Kupracz, L.; Kirshning, A. Beilstein J. Org. Chem. 2013, 9, 1745
27. (f) Wojcik, F.; ÒBrien, A. G.; Gotze, S.; Seeberger, P. H.; Hartmann, L. Chem.-Eur. J. 2013, 19, 3090.
28. (a) Maeda, H.; Mukae, H.; Mizuno, K. Chem. Lett. 2005, 34, 66
29. (b) Sakeda, K.; Wakabayashi, K.; Matsushita, Y.; Ichimura, T.; Suzuki, T.; Wada, T.; Inoue, Y. J. Photochem. Photobiol. A: Chem. 2007, 192, 166.
30. (a) Tsutsumi, K.; Terao, K.; Yamaguchi, H.; Yoshimura, S.; Morimoto, T.; Kakiuchi, K.; Fukuyama, T.; Ryu, I. Chem. Lett. 2010, 16, 7448
31. (b) Terao. K.; Nishiyama, Y.; Aida, S.; Tanimoto, H.; Morimoto, T.; Kakiuchi. K. J. Photo-chem. Photobiol. A: Chem. 2012, 242, 13.
32. Terao, K.; Nishiyama, Y.; Tanimoto, H.; Morimoto, T.; Oelgemöller, M.; Kakiuchi, K. J. Flow Chem. 2012, 2, 73.
33. Yavorskyy, A.; Shvydkiv, O.; Limburq, C.; Nolan, K.; Delaure, Y. M. C.; Oelgemöller, M. Green Chem. 2012, 14, 888.
34. Gotthardt, H.; Lenz, W. Angew. Chem. Int. Ed. 1979, 18, 868.
35. (a) Bach, T. Synthesis 1998, 683
36. (b) D̀Auria, M.; Racioppi, R. Molecules 2013, 18, 11384.
37. Shen, B.; Jamison, T. F. Aust. J. Chem. 2013, 66, 157
38. From the catalogue, Seishin Enterprise Co., Ltd. http://www. betterseishin. co.jp/download/pdf/kussetu.pdf
39. From the catalogue, Wako Pure Chemical Industries Ltd. http://www. siyaku.com/uh/Shs.do?dspCode=W01W0120-0187
40. (a) Burns, J. R.; Ramshaw, C. Lab Chip 2001, 1, 10
41. (b) Fries, D. M.; Waelchli, S.; Rudolf von Rohr, P. Chem. Eng. J. 2008, 135S, S37.
42. Su, J.; Ju, J.; Ji, L.; Zhang, L.; Xu, N. Ind. Eng. Chem. Res. 2008, 47, 1398.