A tin-free route to trans -Diels-Alder motifs by visible light photoredox catalysis

Journal of Organic Chemistry

Volumn 80, Issue 6, 2015, Pages 3309-3314

  Lee, Jun Hee ^a,b   Mho, Sun Il ^a  

^a Ajou University   (South Korea)

^b Institute for Basic Science   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DEHALOGENATION; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL); TIN;

DIASTEREOSELECTIVITIES; MILD REACTION CONDITIONS; PHOTO-CATALYTIC; PHOTOREDOX CATALYSIS; POLYCYCLIC SYSTEMS; REDUCTIVE DEHALOGENATION; STEREOSELECTIVE CONSTRUCTION; STEREOSELECTIVE SYNTHESIS;

LIGHT;

CHEMICAL COMPOUND; DIMETHYL SULFOXIDE; HALOKETONE; OCTALONE DERIVATIVE; POLYCYCLIC COMPOUND; TIN; UNCLASSIFIED DRUG; POLYCYCLIC HYDROCARBON;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEHALOGENATION; DIELS ALDER REACTION; LIGHT; LIGHT EMITTING DIODE; PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; REDUCTION; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; CATALYSIS; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; STEREOISOMERISM;

CATALYSIS; LIGHT; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 84925353199     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b00041     Document Type: Article

References (38)

1. Kim, W. H.; Lee, J. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 12576-12578
2. Kim, W. H.; Lee, J. H.; Aussedat, B.; Danishefsky, S. J. Tetrahedron 2010, 66, 6391-6398
3. Lee, J. H.; Kim, W. H.; Danishefsky, S. J. Tetrahedron Lett. 2010, 51, 4653-4654
4. Shibatomi, K.; Futatsugi, K.; Kobayashi, F.; Iwasa, S.; Yamamoto, H. J. Am. Chem. Soc. 2010, 132, 5625-5627
5. Lee, J. H.; Zhang, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2010, 132, 14330-14333
6. For the trans -Diels-Alder paradigm by the reductive alkylation of α-cyanoketones, see: Peng, F.; Grote, R. E.; Danishefsky, S. J. Tetrahedron Lett. 2011, 521, 3957-3959
7. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854-2867
8. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756-8757
9. Maji, T.; Karmakar, A.; Reiser, O. J. Org. Chem. 2011, 76, 736-739
10. Newmann, M.; Fuldner, S.; Konig, B.; Zeiter, K. Angew. Chem., Int. Ed. 2011, 50, 951-954
11. Douglas, J. J.; Nguyen, J. D.; Cole, K. P.; Stephenson, C. R. J. Aldrichimica Acta 2014, 47, 15-25
12. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176
13. Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387-2403
14. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
15. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
16. Teply, F. Collect. Czech. Chem. Commun. 2011, 76, 859-917
17. Choi, S.; Kim, Y. J.; Kim, S. M.; Yang, J. W.; Kim, S. W.; Cho, E. J. Nat. Commun., doi: 10.1038/ncomms5881.
18. Muller, D. S.; Untiedt, N. L.; Dieskau, A. P.; Lackner, G. L.; Overman, L. E. J. Am. Chem. Soc. 2015, 137, 660-663
19. Hartmann, M.; Li, Y.; Studer, A. J. Am. Chem. Soc. 2012, 134, 16516-16519
20. Zimmerman, J. R.; Manpadi, M.; Spatney, R. Green Chem. 2011, 13, 3103-3106
21. Gong, H.; Andrews, S. A.; Zuccarello, J. L.; Lee, S. J.; Gagné, M. R. Org. Lett. 2009, 11, 879-882
22. Kim, S.; Kim, S. Bull. Chem. Soc. Jpn. 2007, 80, 809-822
23. For further discussion about Hammond's postulate, see: Jackson, R. A. Mechanisms in Organic Reactions; Royal Society of Chemistry: 2004.
24. During the course of this investigation, the Ru-porphyrin-catalyzed Diels-Alder reaction of cyclohexenones with 1,3-butadienes and subsequent epimerization of the cis -fused cycloadducts to the trans -fused isomers were reported: Terada, T.; Kurahashi, T.; Matsubara, S. Org. Lett. 2014, 16, 2594-2597
25. For the preparation of related reference cis -fused octalones, see: Lee, J. H.; Kim, W. H.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 5482-5484
26. Metzger, P.; Casadevall, E.; Pouet, M. J. Org. Magn. Reson. 1982, 19, 229-234
27. 13C NMR spectra with those of the cis -fused compound; see: Richardson, B. M.; Welker, M. E. J. Org. Chem. 1997, 62, 1299-1304
28. Tarantino, K. T.; Liu, P.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 10022-10025
29. Kim, H.; Lee, C. Angew. Chem., Int. Ed. 2012, 51, 12303-12306
30. Nguyen, J. D.; D'Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2012, 4, 854-859
31. Ju, X.; Liang, Y.; Jia, P.; Li, W.; Yu, W. Org. Biomol. Chem. 2012, 10, 498-501
32. Larraufie, M.-H.; Pellet, R.; Fensterbank, L.; Goddard, J.-P.; Lacôte, E.; Malacria, M.; Ollivier, C. Angew. Chem., Int. Ed. 2011, 50, 4463-4466
33. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274-7276
34. Backvall, J.-E.; Ericsson, A. J. Org. Chem. 1994, 59, 5850-5851
35. Peng, F.; Grote, R. E.; Wilson, R. M.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 10904-10909
36. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355-360
37. Hari, D. P.; Konig, B. Chem. Commun. 2014, 50, 6688-6699
38. Cheung, L. L. W.; Yudin, A. K. Chem.-Eur. J. 2010, 16, 4100-4109