Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates

ACS Catalysis

Volumn 6, Issue 9, 2016, Pages 6207-6213

  Hethcox, J Caleb ^a   Shockley, Samantha E ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84984917731     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b01886     Document Type: Short Survey

References (33)

1. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422 10.1021/cr9409804
2. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2944 10.1021/cr020027w
3. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258-297 10.1002/anie.200605113
4. Milhau, L.; Guiry, P. J. Top. Organomet. Chem. 2011, 38, 95-154 10.1007/3418-2011-9
5. Prétôt, R.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 323-325 10.1002/(SICI)1521-3773(19980216)37:3<323::AID-ANIE323>3.3.CO;2-K
6. Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681-1687 10.1021/ja973150r
7. You, S.-L.; Zhu, X.-Z.; Luo, Y.-M.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2001, 123, 7471-7472 10.1021/ja016121w
8. Zheng, W.-H.; Sun, N.; Hou, X.-L. Org. Lett. 2005, 7, 5151-5154 10.1021/ol051882f
9. Zheng, W.-H.; Zheng, B.-H.; Zhang, Y.; Hou, X.-L. J. Am. Chem. Soc. 2007, 129, 7718-7719 10.1021/ja071098l
10. Liu, W.; Chen, D.; Zhu, X.-Z.; Wan, X.-L.; Hou, X.-L. J. Am. Chem. Soc. 2009, 131, 8734-8735 10.1021/ja902410w
11. Fang, P.; Ding, C.-H.; Hou, X.-L.; Dai, L.-X. Tetrahedron: Asymmetry 2010, 21, 1176-1178 10.1016/j.tetasy.2010.03.045
12. Chen, J.-P.; Ding, C.-H.; Liu, W.; Hou, X.-L.; Dai, L.-X. J. Am. Chem. Soc. 2010, 132, 15493-15495 10.1021/ja106703y
13. Takeuchi, R.; Kashio, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 263-265 10.1002/anie.199702631
14. Janssen, J. P.; Helmchen, G. Tetrahedron Lett. 1997, 38, 8025-8026 10.1016/S0040-4039(97)10220-9
15. Helmchen, G.; Dahnz, A.; Dübon, P.; Schelwies, M.; Weihofen, R. Chem. Commun. 2007, 675-691 10.1039/B614169B
16. Hartwig, J. F.; Pouy, M. J. Top. Organomet. Chem. 2011, 34, 169-208 10.1007/978-3-642-15334-1-7
17. Liu, W.-B.; Xia, J.-B.; You, S.-L. Top. Organomet. Chem. 2011, 38, 155-208 10.1007/3418-2011-10
18. Madrahimov, S. T.; Markovic, D.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7228-7229 10.1021/ja902609g
19. Spiess, S.; Raskatov, J. A.; Gnamm, C.; Brödner, K.; Helmchen, G. Chem.-Eur. J. 2009, 15, 11087-11090 10.1002/chem.200902065
20. Hartwig, J. F.; Stanley, L. M. Acc. Chem. Res. 2010, 43, 1461-1475 10.1021/ar100047x
21. Liu, W.-B.; Zheng, C.; Zhuo, C.-X.; Dai, L.-X.; You, S.-L. J. Am. Chem. Soc. 2012, 134, 4812-4821 10.1021/ja210923k
22. Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, K. Angew. Chem., Int. Ed. 2003, 42, 2054-2056 10.1002/anie.200250654
23. Liu, W.-B.; Reeves, C. M.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 17298-17301 10.1021/ja4097829
24. Jiang, X.; Chen, W.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 5819-5823 10.1002/anie.201600235
25. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2068-2071 10.1021/ja311363a
26. Chen, W.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 377-382 10.1021/ja410650e
27. Liu, W.-B.; Reeves, C. M.; Virgil, S. C.; Stoltz, B. M. J. Am. Chem. Soc. 2013, 135, 10626-10629 10.1021/ja4052075
28. Liu, W.-B.; Okamoto, N.; Alexy, E. J.; Hong, A. Y.; Tran, K.; Stoltz, B. M. J. Am. Chem. Soc. 2016, 138, 5234-5237 10.1021/jacs.6b02153
29. Chen, W.; Chen, M.; Hartwig, J. F. J. Am. Chem. Soc. 2014, 136, 15825-15828 10.1021/ja506500u
30. Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633-658 10.1039/c2sc00907b
31. Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065-1068 10.1126/science.1237068
32. Krautwald, S.; Schafroth, M. A.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020-3023 10.1021/ja5003247
33. Sandmeier, T.; Krautwald, S.; Zipfel, H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363-14367 10.1002/anie.201506933