Stereodivergent allylic substitutions with aryl acetic acid esters by synergistic iridium and lewis base catalysis

Journal of the American Chemical Society

Volumn 139, Issue 1, 2017, Pages 87-90

  Jiang, Xingyu ^a   Beiger, Jason J ^a   Hartwig, John F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYSIS; ESTERS; IRIDIUM; IRIDIUM COMPOUNDS; ISOMERS; ORGANIC ACIDS; PH; SUBSTITUTION REACTIONS;

ACTIVATED ESTER; ALLYLIC SUBSTITUTION; ASYMMETRIC CATALYSIS; CHIRAL CATALYST; CHIRAL MOLECULE; DIASTEREO-SELECTIVITY; IRIDIUM COMPLEX; UNIFIED METHOD;

STEREOCHEMISTRY;

ACETIC ACID ESTER; ALLYL COMPOUND; AMIDE; CARBOXYLIC ACID; ESTER; IRIDIUM COMPLEX; LEWIS BASE; ACETIC ACID DERIVATIVE; IRIDIUM; ORGANOMETALLIC COMPOUND;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; STEREOISOMERISM; CHEMISTRY; SYNTHESIS;

ACETATES; ALLYL COMPOUNDS; AMIDES; CARBOXYLIC ACIDS; CATALYSIS; ESTERS; IRIDIUM; LEWIS BASES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 85015807833     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b11692     Document Type: Article

References (54)

1. For selected reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
2. (b) Heimchen, G.; Dahnz, A.; Dubon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675.
3. (c) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258.
4. (d) Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461.
5. (e) Tosatti, P.; Nelson, A.; Marsden, S. P. Org. Biomol. Chem. 2012, 10, 3147.
6. (f) Oliver, S.; Evans, P. A. Synthesis 2013, 45, 3179.
7. (g) Liu, Y.; Han, S.-J.; Liu, W.-B.; Stoltz, B. M. Acc. Chem. Res. 2015, 48, 740.
8. For selected recent publications, see: (a) Trost, B. M.; Miller, J. R.; Hoffman, C. M. J. Am. Chem. Soc. 2011, 133, 8165.
9. (b) Chen, W.; Hartwig, J. V. J. Am. Chem. Soc. 2013, 135, 2068.
10. (c) Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 377.
11. (d) Liu, W.-B.; Reeves, C. M.; Stoltz, B, M. J. Am. Chem. Soc. 2013, 135, 17298.
12. (e) Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626.
13. (f) Chen, W.; Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 15825.
14. (g) Grassi, D.; Alexakis, A Chem. Sci. 2014, 5, 3803.
15. (h) Zhang, X.; Liu, W.-B.; Tu, H.-F.; You, S.-L. Chem. Sci. 2015, 6, 4525.
16. (i) Zhuo, C.-X.; Cheng, Q.; Liu, W.-B.; Zhao, Q.; You, S.-L. Angew. Chem., Int. Ed. 2015, 54, 8475.
17. (j) Jiang, X.; Chen, W.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 5819.
18. (k) Liu, W.-B.; Okamoto, N.; Alexy, E. J.; Hong, A Y.; Tran, K.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 5234.
19. Wu, Q.-F.; Zheng, C.; Zhuo, C.-X.; You, S.-L. Chem. Sci. 2016, 7, 4453.
20. (a) Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065.
21. (b) Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
22. (c) Næsborg, L.; Halskov, K. S.; Tur, F.; Monsted, S. M. N,; Jorgensen, K. A Angew. Chem., Int. Ed. 2015, 54, 10193.
23. (d) Sandmeier, T.; Krautwald, S.; Zipfel H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363.
24. Huo, X.; He, R.; Zhang, X.; Zhang, W. J. Am. Chem. Soc. 2016, 138, 11093.
25. For selected publications that give access to all stereoisomers of the products, see: (a) Huang, Y.; Walji, A M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
26. (b) Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 11586.
27. (c) Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem. Soc. 2008, 130, 14362.
28. (d) Nojiri, A.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 3779.
29. (e) Simmons, B.; Walji, A. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2009, 48, 4349.
30. (f) Mclnturff, E. L.; Yamaguchi, E.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 20628.
31. (g) Shi, S.-L.; Wong, Z. L.; Buchwald, S. L. Nature 2016, 532, 353.
32. (a) Madrahimov, S. T.; Markovic, D.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7228.
33. (b) Madrahimov, S. T.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 8136.
34. (c) Chen, M.; Hartwig, J. V. J. Am. Chem. Soc. 2015, 137, 13972.
35. (d) Madrahimov, S. T.; Li, Q.; Sharma, A.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 14968.
36. (a) Ohmura, T.; Hartwig, J. V. J. Am. Chem. Soc. 2002, 124, 15164.
37. (b) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272.
38. (a) Gaunt, M. J.; Johansson, C. C. C. Chem. Rev. 2007, 107, 5596.
39. (b) Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560.
40. (c) Pauli, D. H.; Weatherwax, A.; Lectka, T. Tetrahedron 2009, 65, 6771.
41. (d) Morrill, L. C.; Smith, A. D. Chem. Soc. Rev. 2014, 43, 6214.
42. For selected reviews of synergistic catalysis, see: (a) Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010, 2010, 2999.
43. (b) Allen, A E.; MacMillan, D.-W. C. Chem. Sci. 2012, 3, 633.
44. (c) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337.
45. For selected publications, see: (a) Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 1810.
46. (b) Liu, G.; Shirley, M. E.; Van, K. N.; McFarlin, R. L.; Romo, D. Nat. Chem. 2013, 5, 1049.
47. (c) Fugard, A J.; Thompson, B. K.; Slawin, A M. Z.; Taylor, J. E.; Smith, A. D. Org. Lett. 2015, 17, 5824.
48. Lee, S. Y.; Neufeind, S.; Fu, G. C. J. Am. Chem. Soc. 2014, 136, 8899.
49. Kawanaka, Y.; Phillips, E. M.; Scheidt, K. A J. Am. Chem. Soc. 2009, 131, 18028.
50. West, T. H.; Daniels, D. S. B.; Slawin, A M. Z.; Smith, A D. J. Am Chem. Soc. 2014, 136, 4476.
51. Schwarz, K. J.; Amos, J. L.; Klein, J. C.; Do, D. T.; Snaddon, T. N. J. Am. Chem. Soc. 2016, 138, 5214.
52. Birman, V. B.; Li, X. Org. Lett. 2006, 8, 1351.
53. (a) Liu, P.; Yang, X.; Birman, V. B.; Houk, K. N. Org. Lett. 2012, 14, 3288.
54. (b) Robinson, E. R. T.; Walden, D. M.; Fallan, C.; Greenhalgh, M. D.; Cheong, P. H.-Y.; Smith, A. D. Chem. Sci. 2016, 7, 6919.