Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Journal of the American Chemical Society

Volumn 136, Issue 1, 2014, Pages 76-79

  Jang, Ki Po ^a   Hutson, Gerri E ^a   Johnston, Ryne C ^b   McCusker, Elizabeth O ^a   Cheong, Paul H Y ^b   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYROLACTONES; COMPUTATIONAL MODEL; N-HETEROCYCLIC CARBENES; PHOSPHONATES; RATIONAL DESIGN; TRANSITION STATE;

CATALYSTS;

ORGANIC COMPOUNDS;

ALDEHYDE DERIVATIVE; CARBENE; GAMMA BUTYROLACTONE; PHOSPHONIC ACID DERIVATIVE;

ADDITION REACTION; ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; ENANTIOSELECTIVITY; MATHEMATICAL MODEL; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

ACYLATION; ALCOHOLS; ALKENES; CATALYSIS; COMPUTER SIMULATION; HETEROCYCLIC COMPOUNDS; HYDROXYLATION; METHANE; MODELS, CHEMICAL; ORGANOPHOSPHONATES;

EID: 84892177661     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja410932t     Document Type: Article

References (55)

1. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
2. Phillips, E. M.; Chan, A.; Scheidt, K. A. Aldrichimica Acta 2009, 43, 55
3. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182
4. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
5. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
6. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Sreekumar, V. Chem. Soc. Rev. 2011, 40, 5336
7. Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
8. Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
9. He, M.; Bode, J. W. Org. Lett. 2005, 7, 3131
10. Chan, A.; Scheidt, K. A. Org. Lett. 2005, 7, 905
11. Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736
12. Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334
13. Phillips, E. M.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416
14. Nair, V.; Babu, B. P.; Vellalath, S.; Varghese, V.; Raveendran, A. E.; Suresh, E. Org. Lett. 2009, 11, 2507
15. Izquierdo, J.; Orue, A.; Scheidt, K. A. J. Am. Chem. Soc. 2013, 135, 10634
16. Nair, V.; Varghese, V.; Babu, B. P.; Sinu, C. R.; Suresh, E. Org. Biomol. Chem. 2010, 8, 761
17. Raup, D. E. A.; Cardinal-David, B.; Holte, D.; Scheidt, K. A. Nat. Chem. 2010, 2, 766
18. Zhao, X. D.; DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 12466
19. Burstein, C.; Tschan, S.; Xie, X. L.; Glorius, F. Synthesis 2006, 2418
20. Nair, V.; Vellalath, S.; Poonoth, M.; Mohan, R.; Suresh, E. Org. Lett. 2006, 8, 507
21. Li, Y.; Zhao, Z. A.; He, H.; You, S. L. Adv. Synth. Catal. 2008, 350, 1885
22. Rommel, M.; Fukuzumi, T.; Bode, J. W. J. Am. Chem. Soc. 2008, 130, 17266
23. Lv, H.; Tiwari, B.; Mo, J. M.; Xing, C.; Chi, Y. R. Org. Lett. 2012, 14, 5412
24. Sun, L. H.; Shen, L. T.; Ye, S. Chem. Commun. 2011, 47, 10136
25. Cohen, D. T.; Scheidt, K. A. Chem. Sci. 2012, 3, 53
26. Dugal-Tessier, J.; O'Bryan, E. A.; Schroeder, T. B. H.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 4963
27. Mo, J. M.; Chen, X. K.; Chi, Y. R. J. Am. Chem. Soc. 2012, 134, 8810
28. Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1998, 120, 4895
29. Evans, D. A.; Scheidt, K. A.; Fandrick, K. R.; Lam, H. W.; Wu, J. J. Am. Chem. Soc. 2003, 125, 10780
30. Takenaka, N.; Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 742
31. Collinsova, M.; Jiracek, J. Curr. Med. Chem. 2000, 7, 629
32. Kafarski, P.; Lejczak, B. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 301
33. Mucha, A.; Kafarski, P.; Berlicki, L. J. Med. Chem. 2011, 54, 5955
34. Kolodiazhny, O. I. Tetrahedron: Asymmetry 2005, 16, 3295
35. Samanta, S.; Zhao, C. G. J. Am. Chem. Soc. 2006, 128, 7442
36. Gondi, V. B.; Hagihara, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2009, 48, 776
37. Hou, G.; Yu, J.; Yu, C.; Wu, G.; Miao, Z. Adv. Synth. Catal. 2013, 355, 589
38. Corbett, M. T.; Johnson, J. S. J. Am. Chem. Soc. 2013, 135, 594
39. Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102
40. Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 10521
41. Vicario, J.; Ezpeleta, J. M.; Palacios, F. Adv. Synth. Catal. 2012, 354, 2641
42. Lee, K.-s.; Zhugralin, A. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7253
43. Harper, K. C.; Sigman, M. S. J. Org. Chem. 2013, 78, 2813
44. Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
45. Frisch, M. J.; Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
46. Johnston, R. C.; Cheong, P. H. Org. Biomol. Chem. 2013, 11, 5057
47. Bryan, P.; Pantoliano, M. W.; Quill, S. G.; Hsiao, H. Y.; Poulos, T. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 3743
48. Stetter, H. Angew. Chem., Int. Ed. 1976, 15, 639
49. Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899
50. de Alaniz, J. R.; Rovis, T. Synlett 2009, 1189
51. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2011, 133, 10402
52. Sánchez-Larios, E.; Thai, K.; Bilodeau, F.; Gravel, M. Org. Lett. 2011, 13, 4942
53. Fang, X. Q.; Chen, X. K.; Lv, H.; Chi, Y. R. Angew. Chem., Int. Ed. 2011, 50, 11782
54. DiRocco, D. A.; Noey, E. L.; Houk, K. N.; Rovis, T. Angew. Chem., Int. Ed. 2012, 51, 2391
55. For a recent example of an intermolecular enantioselective Stetter reaction with a β-alkyl substitution at 59% yield and 90:10 er, see: Wurz, N. E.; Daniliuc, C. G.; Glorius, F. Chem.-Eur. J. 2012, 18, 16297