Extraordinary microwave effect on atropo-enantioselective catalytic reduction of biaryl lactones

Chemistry Letters

Volumn 42, Issue 2, 2013, Pages 165-167

  Nushiro, Kazuya ^a   Kikuchi, Satoshi ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84873973186     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2013.165     Document Type: Review

References (30)

1. a) C. O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, WIELY-VCH, Weinheim, 2005. doi:10.1002/3527606556.
2. b) D. Bogdal, Microwave-Assisted Organic Synthesis, Elsevier, San Diego, 2005.
3. Microwaves in Organic Synthesis, ed. by A. Loupy, WIELY-VCH, Weinheim, 2006, Vol. 2.
4. Microwave-Assisted Synthesis of Heterocycles, ed. by E. van der Eycken, C. O. Kappe, Springer, Berlin, 2006. doi:10.1007/11497363.
5. e) J. P. Tierney, P. Lidström, Microwave Assisted Organic Synthesis, Blackwell Publishing, Oxford, 2007.
6. f) C. O. Kappe, D. Dallinger, S. S. Murphree, Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols, WIELY-VCH, Weinheim, 2009. doi:10.1002/ 9783527623907.
7. g) A. de la Hoz, A. Díaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164.
8. h) S. Caddick, R. Fitzmaurice, Tetrahedron 2009, 65, 3325.
9. a) M. Hosseini, N. Stiasni, V. Barbieri, C. O. Kappe, J. Org. Chem. 2007, 72, 1417.
10. b) M. A. Herrero, J. M. Kremsner, C. O. Kappe, J. Org. Chem. 2008, 73, 36.
11. c) J. Ramier, E. Renard, D. Grande, Macromol. Chem. Phys. 2012, 213, 784.
12. Microwave Heating as a Tool for Sustainable Chemistry, ed. by N. E. Leadbeater, CRC Press, New York, 2010, pp. 59.
13. e) J. R. Schmink, N. E. Leadbeater, Org. Biomol. Chem. 2009, 7, 3842.
14. f) H. Shimizu, Y. Yoshimura, H. Hinou, S.-I. Nishimura, Tetrahedron 2008, 64, 10091.
15. g) S. Horikoshi, N. Serpone, J. Photochem. Photobiol., C 2009, 10, 96.
16. h) A. M. Rodriguez, C. Cebrián, P. Prieto, J. I. García, A. de la Hoz, A. Díaz-Ortiz, Chem.-Eur. J. 2012, 18, 6217.
17. a) T. Ashizawa, T. Yamada, Chem. Lett. 2009, 38, 246.
18. b) S. Kikuchi, T. Tsubo, T. Ashizawa, T. Yamada, Chem. Lett. 2010, 39, 574.
19. T. Ashizawa, S. Tanaka, T. Yamada, Org. Lett. 2008, 10, 2521.
20. a)G.Bringmann, T. Hartung, Angew. Chem. 1992, 104, 782
21. G. Bringmann, T. Hartung, Angew. Chem., Int. Ed. Engl. 1992, 31, 761.
22. b) G. Bringmann, S. Tasler, R.-M. Pfeifer, M. Breuning, J. Organomet. Chem. 2002, 661, 49.
23. c) G. Bringmann, M. Breuning, P. Henschel, J. Hinrichs, Org. Synth. 2002, 79, 72.
24. d) G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518
25. G. Bringmann, A. J. P. Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem., Int. Ed. 2005, 44, 5384.
26. a) This starting material was synthesized according to the literature, see: G. Bringmann, M. Heubes, M. Breuning, L. Göbel, M. Ochse, B. Schöner, O. Schupp, J. Org. Chem. 2000, 65, 722.
27. b) G. Bringmann, J. Hinrichs, J. Kraus, A. Wuzik, T. Schulz, J. Org. Chem. 2000, 65, 2517.
28. C. Gabriel, S. Gabriel, E. H. Grant, B. S. J. Halstead, D. M. P. Mingos, Chem. Soc. Rev. 1998, 27, 213.
29. We performed the reaction of 1e at 50 °C, summarized in the Supporting Information.12
30. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.