Asymmetric α-photoalkylation of β-ketocarbonyls by primary amine catalysis: Facile access to acyclic all-carbon quaternary stereocenters

Journal of the American Chemical Society

Volumn 136, Issue 42, 2014, Pages 14642-14645

  Zhu, Yunbo ^a,b   Zhang, Long ^a,b   Luo, Sanzhong ^a,b  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b Key Laboratory of Photoelectronic Thin Film Devices and Technology of Tianjin   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FACILE ACCESS; PRIMARY AMINES; QUATERNARY STEREOCENTERS;

AMINE; CARBON; CARBONYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; OLIGOMERIZATION; PHOTOALKYLATION; SCREENING;

EID: 84908377191     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508605a     Document Type: Article

References (59)

1. Marek, I.; Minko, Y.; Pasco, M.; Mejuch, T.; Gilboa, N.; Chechik, H.; Das, P. J. J. Am. Chem. Soc. 2014, 136, 2682
2. Alba, A. N.; Viciano, M.; Rios, R. ChemCatChem 2009, 1, 437
3. Vesely, J.; Rios, R. ChemCatChem 2012, 4, 942
4. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450
5. Xie, H.; Zu, L.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886
6. Bengoa, E. G.; Landa, A.; Lizarraga, A.; Mielgo, A.; Oiarbide, M.; Palomo, C. Chem. Sci. 2011, 2, 353
7. Ibrahem, I.; Zhao, G. L.; Rios, R.; Vesely, J.; Sundén, H.; Dziedzic, P.; Córdova, A. Chem.-Eur. J. 2008, 14, 7867
8. Companyó, X.; Alba, A. N.; Cárdenas, F.; Moyano, A.; Rios, R. Eur. J. Org. Chem. 2009, 3075
9. Beeson, T. D.; Mastracchio, A.; Hong, J. B.; Ashton, K.; MacMillan, D. W. C. Science 2007, 316, 582
10. Jang, H. Y.; Hong, J. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2007, 129, 7004
11. Graham, T. H.; Jones, C. M.; Jui, N. T.; MacMillan, D. W. C. J. Am. Chem. Soc. 2008, 130, 16494
12. Wilson, J. E.; Casarez, A. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 11332
13. Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, Giuseppe.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8707
14. Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew.Chem. Int. Ed. 2009, 48, 1313
15. Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 62
16. Doyle, A. G.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 3701
17. Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 5604
18. Minko, Y.; Pasco, M.; Lercher, L.; Botoshansky, M.; Marek, I. Nature 2012, 490, 522
19. Boeckman, R. K.; Boehmler, D. J.; Musselman, R. A. Org. Lett. 2001, 3, 3777
20. Arpin, A.; Manthorpe, J. M.; Gleason, J. L. Org. Lett. 2006, 8, 1359
21. Li, H. M.; Song, J.; Liu, X. F.; Deng, L. J. Am. Chem. Soc. 2005, 127, 8948
22. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto J. Am. Chem. Soc. 2005, 127, 119
23. Hamashima, Y.; Hotta, D.; Sodeoka J. Am. Chem. Soc. 2002, 124, 11240
24. Rigby, C. L.; Dixon, D. J. Chem. Commun. 2008, 3798
25. Zhang, Z. H.; Dong, X. Q.; Chen, D.; Wang, C. J. Chem.-Eur. J. 2008, 14, 8780
26. List, B.; Coric, I.; Grygorenko, O.; Kaib, P.; Komarov, I.; Lee, A.; Leutzsh, M.; Pan, S. C.; Tymtsunik, A. V.; van Gemmeren, M. Angew. Chem., Int. Ed. 2014, 53, 282
27. Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065
28. Brown, A. R.; Kuo, W. H.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286
29. Lalonde, M. P.; Chen, Y. G.; Jacobson, E. N. Angew. Chem., Int. Ed. 2006, 45, 6366
30. Ting, Y. F.; Chang, C. L.; Reddy, R. J.; Magar, D. R.; Chen, K. Chem.-Eur. J. 2010, 16, 7030
31. Zhu, Q.; Lu, Y. X. Chem. Commun. 2010, 46, 2235
32. Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F., III Org. Lett. 2004, 6, 2527
33. Belot, S.; Massaro, A.; Tenti, A.; Mordini, A.; Alexakis, A. Org. Lett. 2008, 10, 4557
34. Enders, D.; Wang, C.; Bats, J. Angew. Chem., Int. Ed. 2008, 47, 7539
35. Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139
36. Müller, C.; Bauer, A.; Maturi, M. M.; Cuquerella, M. C.; Miranda, M. A.; Bach, T. J. Am. Chem. Soc. 2011, 133, 16689
37. Alonso, R.; Bach, T. Angew. Chem., Int. Ed. 2014, 53, 4368
38. Müller, C.; Bauer, A.; Bach, T. Angew. Chem., Int. Ed. 2009, 48, 6640
39. Maturi, M. M.; Bach, T. Angew. Chem., Int. Ed. 2014, 53, 7661
40. Vallavoju, N.; Selvakumar, S.; Jockusch, S.; Sibi, M. P.; Sivaguru, J. Angew. Chem., Int. Ed. 2014, 53, 5604
41. Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77
42. Shih, H. W.; Vander Wal, M. N.; Grange, R. L.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 13600
43. Neumann, M.; Füldner, S.; König, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951
44. Riente, P.; Adams, A. M.; Albero, J.; Palomares, E.; Pericas, M. A. Angew. Chem., Int. Ed. 2014, 53, 9613
45. Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 1360
46. Arceo, E.; Jurberg, L. D.; álvarez-Fernández, A.; Melchiorre, P. Nat. Chem. 2013, 5, 750
47. Arceo, E.; Bahamonde, A.; Bergonzini, G.; Melchiorre, P. Chem. Sci. 2014, 5, 2438
48. Xu, C.; Zhang, L.; Luo, S. Angew. Chem., Int. Ed. 2014, 53, 4149
49. Müller, K.; Previdoli, F.; Desilvestro, H. Helv. Chim. Acta 1981, 64, 2497
50. Lide, D. R. Handbook of Chemistry and Physics; CRC Press: New York, 1995; ed. 76, p 220.
51. Zhang, L.; Luo, S. Synlett 2012, 1575
52. Hunziker, D.; Neidhart, W. U.S. Patent US20120245191, September 27, 2012.
53. Hunziker, D.; Neidhart, W. Patent WO2012123432, September 20, 2012.
54. Sarma, K. D.; Zhang, J.; Huang, Y.; Davidson Eur. J. Org. Chem. 2006, 3730
55. - anion, if not completely excluded, should be minor. For a recent discussion: Fu, N.; Zhang, L.; Luo, S.; Cheng, J.-P. Chem.-Eur. J. 2013, 19, 15669-15681
56. Penning, M.; Christoffers, J. Eur. J. Org. Chem. 2013, 389
57. Hasegawa, T.; Yang, Y.; Kikuchi, S.; Nakamura, T.; Maeda, Y. J. Phys. Org. Chem. 2006, 19, 122
58. Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; McGrath, J. M.; Schott, H. N.; Zepp, R. G. J. Am. Chem. Soc. 1972, 94, 7506
59. Hasegawa, T.; Nishimura, M.; Yoshioka, M. J. Phys. Org. Chem. 1990, 3, 230