Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis

Journal of the American Chemical Society

Volumn 137, Issue 7, 2015, Pages 2452-2455

  Ruiz Espelt, Laura ^a   McPherson, Iain S ^a   Wiensch, Eric M ^a   Yoon, Tehshik P ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; TRANSITION METALS;

AMINO RADICALS; CHIRAL LEWIS ACID; ENANTIOSELECTIVE ADDITION; ENANTIOSELECTIVE CONJUGATE ADDITION; LEWIS ACID CATALYSIS; MICHAEL ACCEPTORS; PHOTOREDOX CATALYSIS; REACTIVE INTERMEDIATE;

CATALYSIS;

LEWIS ACID; RADICAL; TRANSITION ELEMENT; AMINE; FREE RADICAL;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CONJUGATE; ENANTIOSELECTIVITY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; REACTION ANALYSIS; CHEMISTRY; STEREOISOMERISM;

AMINES; CATALYSIS; FREE RADICALS; LEWIS ACIDS; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 84923632877     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512746q     Document Type: Article

References (47)

1. Hoffmann, N. Chem. Rev. 2008, 108, 1052
2. Bach, T.; Hehn, J. P. Angew. Chem., Int. Ed. 2011, 50, 1000
3. Inoue, Y. Chem. Rev. 1992, 92, 741
4. Svoboda, J.; König, B. Chem. Rev. 2006, 106, 5413
5. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
6. Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875
7. Shih, H.-W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
8. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094
9. Rono, L. J.; Yayla, H. G.; Wang, D. Y.; Armstrong, M. F.; Knowles, R. R. J. Am. Chem. Soc. 2013, 135, 17735
10. Du, J.; Skubi, K. L.; Schultz, D. M.; Yoon, T. P. Science 2014, 344, 392
11. Yamamoto, H., Ed. Lewis Acids in Organic Synthesis; Wiley VHC: New York, 2000; Vols. 1 and 2.
12. Ruiz Espelt, L.; Wiensch, E. M.; Yoon, T. P. J. Org. Chem. 2013, 78, 4107
13. Brumfield, M. A.; Quillen, S. L.; Yoon, U. C.; Mariano, P. S. J. Am. Chem. Soc. 1984, 106, 6855
14. Hasegawa, E.; Xu, W.; Mariano, P. S.; Yoon, U.-C.; Kim, J.-U. J. Am. Chem. Soc. 1988, 110, 8099
15. Xu, W.; Yoon, T. J.; Hasegawa, E.; Yoon, U.-C.; Mariano, P. S. J. Am. Chem. Soc. 1989, 111, 406
16. Zhang, X.; Yeh, S.-R.; Hong, S.; Frecero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211
17. Su, Z.; Mariano, P. S.; Falvey, D. E.; Yoon, U.-C.; Oh, S. W. J. Am. Chem. Soc. 1998, 120, 10676
18. Pandey, G.; Kumaraswamy, G.; Bhalerao, U. T. Tetrahedron Lett. 1989, 30, 6059
19. Pandey, G.; Reddy, G. D.; Kumaraswamy, G. Tetrahedron 1994, 50, 8185
20. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
21. Miyake, Y.; Ashida, Y.; Nakajima, K.; Nishibayashi, Y. Chem. Commun. 2012, 48, 6966
22. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672
23. Miyake, Y.; Nakajima, K.; Nishibayashi, Y. J. Am. Chem. Soc. 2012, 134, 3338
24. Zhu, S.; Das, A.; Bui, L.; Zhou, H.; Curran, D. P.; Rueping, M. J. Am. Chem. Soc. 2013, 135, 1823
25. Miyake, Y.; Ashida, Y.; Nakajima, K.; Nishibayashi, Y. Chem.-Eur. J. 2014, 20, 6120
26. Zuo, Z.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257
27. Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437
28. Jung, Y. S.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 4611
29. Pandey, G.; Reddy, G. D.; Chakrabarti, D. J. Chem. Soc., Perkin Trans. 1 1996, 219
30. Pandey, G.; Chakrabarti, D. Tetrahedron Lett. 1996, 37, 2285
31. Pandey, G.; Kapur, M. Synthesis 2001, 1263
32. Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139
33. Evans, D. A.; Rovis, T.; Johnson, J. S. Pure Appl. Chem. 1999, 71, 1407
34. Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033
35. Christoffers, J.; Koripelly, G.; Rosiak, A.; Rössle, M. Synthesis 2007, 1279
36. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 9200
37. Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 7517
38. Sibi, M. P.; Zimmerman, J. J. Am. Chem. Soc. 2006, 128, 13346
39. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029
40. Wu, J. H.; Zhang, G. R.; Porter, N. A. Tetrahedron Lett. 1997, 38, 2067
41. Porter, N. A.; Feng, H.; Kavrakova, I. K. Tetrahedron Lett. 1999, 40, 6713
42. Mariano, P.S., Ed. Advances in Electron Transfer Chemistry; Jai Press: Greenwich, CT, 1994.
43. Sibi has previously described the cleavage of a pyrazolidinone auxiliary using an intramolecular transacylation process: Sibi, M. P.; Liu, M. Org. Lett. 2001, 3, 4181
44. During the preparation of this manuscript, Nishibayashi reported the photocatalytic synthesis of racemic pyrrolidinones by a conceptually similar desilylative conjugate addition-cyclization process: Nakajima, K.; Kitagawa, M.; Ashida, Y.; Miyake, Y.; Nishibayashi, Y. Chem. Commun. 2014, 50, 8900
45. For an excellent review of dramatic halide effects in catalytic reactions, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26
46. Boukhalfa, H.; Crumbliss, A. L. Inorg. Chem. 2001, 40, 4183
47. Biruš, M.; Krznaric, G.; Pribanić, M.; Ursic, S. J. Chem. Res., Synop. 1985, 4