Iridium-Catalyzed Diastereoselective and Enantioselective Allylic Substitutions with Acyclic α-Alkoxy Ketones

Angewandte Chemie - International Edition

Volumn 55, Issue 19, 2016, Pages 5819-5823

  Jiang, Xingyu ^a,b   Chen, Wenyong ^a,b   Hartwig, John F ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

alkylation; asymmetric catalysis; diastereoselectivity; iridium; ketones

Indexed keywords

ALKYLATION; CATALYSIS; ENANTIOSELECTIVITY; IRIDIUM; IRIDIUM COMPOUNDS; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

ASYMMETRIC ALKYLATION; ASYMMETRIC CATALYSIS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE; ENANTIOMERIC PURITY; ENANTIOSELECTIVE ALLYLIC SUBSTITUTION; STEREOGENIC CENTERS; TERTIARY ALCOHOLS;

KETONES;

ALLYL COMPOUND; COORDINATION COMPOUND; COPPER; IRIDIUM; KETONE;

CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALLYL COMPOUNDS; CATALYSIS; COORDINATION COMPLEXES; COPPER; IRIDIUM; KETONES; STEREOISOMERISM;

EID: 84979489496     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201600235     Document Type: Article

References (48)

1. C. H. Ding, X. L. Hou, in Comprehensive Organic Synthesis II, 2 nd ed., (Ed.: P. Knochel,), Elsevier, Amsterdam, 2014, p. 648;
2. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461;
3. Y. Liu, S.-J. Han, W.-B. Liu, B. M. Stoltz, Acc. Chem. Res. 2015, 48, 740;
4. Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258;
5. Angew. Chem. 2008, 120, 264;
6. S. Oliver, P. A. Evans, Synthesis 2013, 3179;
7. B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395.
8. J. Christoffers, A. Baro, Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2005;
9. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363;
10. K. W. Quasdorf, L. E. Overman, Nature 2014, 516, 181;
11. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
12. B. M. Trost, C. Jiang, Synthesis 2006, 369;
13. M. Yus, J. C. González-Gómez, F. Foubelo, Chem. Rev. 2013, 113, 5595.
14. J. F. Hartwig, M. J. Pouy, Top. Organomet. Chem. 2011, 34, 169;
15. G. Helmchen, in Iridium Complexes in Organic Synthesis, Wiley-VCH, Weinheim, 2009, p. 211;
16. G. Helmchen, A. Dahnz, P. Dubon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675;
17. W.-B. Liu, J.-B. Xia, S.-L. You, Top. Organomet. Chem. 2012, 38, 155;
18. J. F. Teichert, B. L. Feringa, Angew. Chem. Int. Ed. 2010, 49, 2486;
19. Angew. Chem. 2010, 122, 2538;
20. P. Tosatti, A. Nelson, S. P. Marsden, Org. Biomol. Chem. 2012, 10, 3147.
21. W. Chen, M. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 15825;
22. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 377;
23. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 2068;
24. W.-B. Liu, C. M. Reeves, S. C. Virgil, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 10626. For reactions of α-branched aldehydes, see
25. S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065;
26. S. Krautwald, M. A. Schafroth, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3020;
27. T. Sandmeier, S. Krautwald, H. F. Zipfel, E. M. Carreira, Angew. Chem. Int. Ed. 2015, 54, 14363;
28. Angew. Chem. 2015, 127, 14571; For reactions of stabilized enolates of β-ketoesters, see
29. W.-B. Liu, C. M. Reeves, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 17298; For related work with molybdenum and palladium, see
30. M. Braun, F. Laicher, T. Meier, Angew. Chem. Int. Ed. 2000, 39, 3494;
31. Angew. Chem. 2000, 112, 3637;
32. J.-P. Chen, C.-H. Ding, W. Liu, X.-L. Hou, L.-X. Dai, J. Am. Chem. Soc. 2010, 132, 15493;
33. B. M. Trost, K. Dogra, M. Franzini, J. Am. Chem. Soc. 2004, 126, 1944;
34. B. M. Trost, J. R. Miller, C. M. Hoffman, J. Am. Chem. Soc. 2011, 133, 8165;
35. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2006, 128, 4590;
36. B. M. Trost, Y. Zhang, J. Am. Chem. Soc. 2007, 129, 14548;
37. W.-H. Zheng, B.-H. Zheng, Y. Zhang, X.-L. Hou, J. Am. Chem. Soc. 2007, 129, 7718.
38. R. Mahrwald, Modern Aldol Reactions, Wiley-VCH, Weinheim, 2004.
39. T. Kanayama, K. Yoshida, H. Miyabe, T. Kimachi, Y. Takemoto, J. Org. Chem. 2003, 68, 6197;
40. U. Kazmaier, F. L. Zumpe, Angew. Chem. Int. Ed. 1999, 38, 1468;
41. Angew. Chem. 1999, 111, 1572;
42. K. Huwig, K. Schultz, U. Kazmaier, Angew. Chem. Int. Ed. 2015, 54, 9120;
43. Angew. Chem. 2015, 127, 9248.
44. P. A. Evans, M. J. Lawler, J. Am. Chem. Soc. 2004, 126, 8642; For related work with α-hydroxy esters, see
45. A. Kiefer, G. Gawas, U. Kazmaier, Eur. J. Org. Chem. 2015, 5810.
46. T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164;
47. C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272.
48. H. Seto, L. N. Mander, Synth. Commun. 1992, 22, 2823.