Enantioselective synthesis of allenes by catalytic traceless petasis reactions

Journal of the American Chemical Society

Volumn 139, Issue 5, 2017, Pages 1998-2005

  Jiang, Yao ^a   Diagne, Abdallah B ^b   Thomson, Regan J ^b   Schaus, Scott E ^a  

^a USA   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; ENANTIOSELECTIVITY; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

ASYMMETRIC SYNTHESIS; CHEMICAL BONDINGS; ENANTIOSELECTIVE; ENANTIOSELECTIVE APPROACH; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC ADDITIONS; REACTIVITY PATTERN; SULFONYL HYDRAZONES;

HYDROCARBONS;

ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; HYDRAZONE DERIVATIVE; ALKADIENE; PHENOL DERIVATIVE;

ALKYNYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MANNICH REACTION; NUCLEOPHILICITY; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKADIENES; BORONIC ACIDS; CATALYSIS; HYDRAZONES; MOLECULAR STRUCTURE; PHENOLS; STEREOISOMERISM;

EID: 85011955153     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b11937     Document Type: Article

References (52)

1. van't Hoff, J. H. La Chimie dans L'Espace; Bazendijk: Rotterdam, 1875.
2. Burton, B. S.; von Pechmann, H. Ber. Dtsch. Chem. Ges. 1887, 20, 145.
3. Jones, E. R. H.; Shaw, B. L.; Whiting, M. C. J. Chem. Soc. 1954, 3212.
4. Crombie, L.; Harper, S. H.; Thompson, D. J. Chem. Soc. 1951, 2906.
5. Hoffmann-Roder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196.
6. Rivera-Fuentes, P.; Diederich, F. Angew. Chem., Int. Ed. 2012, 51, 2818.
7. Ma, S. Chem. Rev. 2005, 105, 2829.
8. Allen, A. D.; Tidwell, T. T. Chem. Rev. 2013, 113, 7287.
9. Yu, S.; Ma, S. Chem. Commun. 2011, 47, 5384.
10. Ogasawara, M. Tetrahedron: Asymmetry 2009, 20, 259.
11. Neff, R. K.; Frantz, D. E. ACS Catal. 2014, 4, 519.
12. Ye, J.; Ma, S. Org. Chem. Front. 2014, 1, 1210.
13. Henderson, M. A.; Heathcock, C. H. J. Org. Chem. 1988, 53, 4736.
14. Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
15. Marshall, J. A.; Robinson, E. D.; Zapata, A. J. Org. Chem. 1989, 54, 5854.
16. Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. J. Am. Chem. Soc. 1990, 112, 8042.
17. Gooding, O. W.; Beard, C. C.; Jackson, D. Y.; Wren, D. L.; Cooper, G. F. J. Org. Chem. 1991, 56, 1083.
18. Marshall, J. A.; Pinney, K. G. J. Org. Chem. 1993, 58, 7180.
19. Pu, X.; Ready, J. M. J. Am. Chem. Soc. 2008, 130, 10874.
20. Tang, X.; Woodward, S.; Krause, N. Eur. J. Org. Chem. 2009, 2009, 2836.
21. Uehling, M. R.; Marionni, S. T.; Lalic, G. Org. Lett. 2012, 14, 362.
22. Wu, S.; Huang, X.; Wu, W.; Li, P.; Fu, C.; Ma, S. Nat. Commun. 2015, 6, 7946.
23. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
24. Lü, R.; Ye, J.; Cao, T.; Chen, B.; Fan, W.; Lin, W.; Liu, J.; Luo, H.; Miao, B.; Ni, S.; Tang, X.; Wang, N.; Wang, Y.; Xie, X.; Yu, Q.; Yuan, W.; Zhang, W.; Zhu, C.; Ma, S. Org. Lett. 2013, 15, 2254.
25. Deska, J.; Backvall, J.-E. Org. Biomol. Chem. 2009, 7, 3379.
26. Ogasawara, M.; Ikeda, H.; Nagano, T.; Hayashi, T. J. Am. Chem. Soc. 2001, 123, 2089.
27. Nishimura, T.; Makino, H.; Nagaosa, M.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 12865.
28. Wang, M.; Liu, Z.-L.; Zhang, X.; Tian, P.-P.; Xu, Y.-H.; Loh, T.-P. J. Am. Chem. Soc. 2015, 137, 14830.
29. Crouch, I. T.; Neff, R. K.; Frantz, D. E. J. Am. Chem. Soc. 2013, 135, 4970.
30. Ye, J.; Li, S.; Chen, B.; Fan, W.; Kuang, J.; Liu, J.; Liu, Y.; Miao, B.; Wan, B.; Wang, Y.; Xie, X.; Yu, Q.; Yuan, W.; Ma, S. Org. Lett. 2012, 14, 1346.
31. Chu, W.-D.; Zhang, L.; Zhang, Z.; Zhou, Q.; Mo, F.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2016, 138, 14558.
32. Trost, B. M.; Fandrick, D. R.; Dinh, D. C. J. Am. Chem. Soc. 2005, 127, 14186.
33. Qian, H.; Yu, X.; Zhang, J.; Sun, J. J. Am. Chem. Soc. 2013, 135, 18020.
34. Liu, H.; Leow, D.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2009, 131, 7212.
35. Hashimoto, T.; Sakata, K.; Tamakuni, F.; Dutton, M. J.; Maruoka, K. Nat. Chem. 2013, 5, 240.
36. Tap, A.; Blond, A.; Wakchaure, V. N.; List, B. Angew. Chem., Int. Ed. 2016, 55, 8962.
37. Mundal, D. A.; Lutz, K. E.; Thomson, R. J. J. Am. Chem. Soc. 2012, 134, 5782.
38. Diagne, A. B.; Li, S.; Perkowski, G. A.; Mrksich, M.; Thomson, R. J. ACS Comb. Sci. 2015, 17, 658.
39. Lou, S.; Schaus, S. E. J. Am. Chem. Soc. 2008, 130, 6922.
40. Bishop, J. A.; Lou, S.; Schaus, S. E. Angew. Chem., Int. Ed. 2009, 48, 4337.
41. Lou, S.; Moquist, P. N.; Schaus, S. E. J. Am. Chem. Soc. 2007, 129, 15398.
42. Muncipinto, G.; Moquist, P. N.; Schreiber, S. L.; Schaus, S. E. Angew. Chem., Int. Ed. 2011, 50, 8172.
43. Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169.
44. Jiang, Y.; Schaus, S. E. Angew. Chem., Int. Ed. 2017, DOI: 10.1002/anie.201611332.
45. Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537.
46. Ye, J.; Fan, W.; Ma, S. Chem.-Eur. J. 2013, 19, 716.
47. Bagby, M. O.; Smith, C. R.; Wolff, I. A. J. Org. Chem. 1965, 30, 4227.
48. Tang, X. J.; Huang, X.; Cao, T.; Han, Y. L.; Jiang, X. G.; Lin, W. L.; Tang, Y.; Zhang, J. S.; Yu, Q.; Fu, C. L.; Ma, S. M. Org. Chem. Front. 2015, 2, 688.
49. Zhang, X.; Fu, C.; Yu, Y.; Ma, S. Chem.-Eur. J. 2012, 18, 13501.
50. Masuzawa, Y.; Tamogami, S.; Kitahara, T. Nat. Prod. Lett. 1999, 13, 239.
51. Xie, H.; Sammis, G. M.; Flamme, E. M.; Kraml, C. M.; Sorensen, E. J. Chem.-Eur. J. 2011, 17, 11131.
52. Movassaghi, M.; Ahmad, O. K. Angew. Chem., Int. Ed. 2008, 47, 8909.