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Angewandte Chemie - International Edition

Volumn 53, Issue 45, 2014, Pages 12172-12176

Iridium-Catalyzed Regio- and Enantioselective Allylic Substitution of Silyl Dienolates Derived from Dioxinones

(2) Chen, Ming a Hartwig, John F a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

alkylation; allylic compounds; asymmetric catalysis; enantioselectivity; iridium

Indexed keywords

ALKYLATION; ALLYLATION; CARBONATES; CATALYSIS; ENANTIOSELECTIVITY; IRIDIUM; ORGANIC SOLVENTS; SUBSTITUTION REACTIONS;

1 ,5-CYCLOOCTADIENE; ALLYLIC COMPOUNDS; ALLYLIC SUBSTITUTION; ASYMMETRIC ALLYLATION; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE ALLYLIC SUBSTITUTION; TETRA-HYDROFURAN; TRIMETHYLSILYL;

IRIDIUM COMPOUNDS;

DIOXIN; IRIDIUM;

CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; DIOXINS; IRIDIUM; STEREOISOMERISM;

EID: 84911489586 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201406778 Document Type: Article

Times cited : (44)

References (76)

1
- 0003445429
- Springer, Berlin
- E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, Vol. I-III, Springer, Berlin, 1999;
- (1999) Comprehensive Asymmetric Catalysis, Vol. I-III
- Jacobsen, E.N.¹ Pfaltz, A.² Yamamoto, H.³

2
- 84891580093
- 2ed nd ed Wiley-VCH, New York
- I. Ojima, Catalytic Asymmetric Synthesis, 2ed nd ed Wiley-VCH, New York, 2000.
- (2000) Catalytic Asymmetric Synthesis
- Ojima, I.¹

3
- 6844254916
- B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395;
- (1996) Chem. Rev. , vol.96 , pp. 395
- Trost, B.M.¹ Van Vranken, D.L.²

4
- 0042379988
- B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
- (2003) Chem. Rev. , vol.103 , pp. 2921
- Trost, B.M.¹ Crawley, M.L.²

5
- 38049017956
- Z. Lu, S. Ma, Angew. Chem. Int. Ed. 2008, 47, 258;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 258
- Lu, Z.¹ Ma, S.²

6
- 53349113487
- Angew. Chem. 2008, 120, 264;
- (2008) Angew. Chem. , vol.120 , pp. 264

7
- 33845579450
- X. Xie, Y. Chen, D. Ma, J. Am. Chem. Soc. 2006, 128, 16050;
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 16050
- Xie, X.¹ Chen, Y.² Ma, D.³

8
- 34547184381
- J. Alemán, B. Richter, K. A. Jørgensen, Angew. Chem. Int. Ed. 2007, 46, 5515;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5515
- Alemán, J.¹ Richter, B.² Jørgensen, K.A.³

9
- 84940459304
- Angew. Chem. 2007, 119, 5611.
- (2007) Angew. Chem. , vol.119 , pp. 5611

10
- 0001019699
- L. Weiler, J. Am. Chem. Soc. 1970, 92, 6702
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 6702
- Weiler, L.¹

11
- 34447295369
- H. Shojaei, Z. Li-Böhmer, P. von Zezschwitz, J. Org. Chem. 2007, 72, 5091;
- (2007) J. Org. Chem. , vol.72 , pp. 5091
- Shojaei, H.¹ Li-Böhmer, Z.² Von Zezschwitz, P.³

12
- 34548725126
- M. A. González, S. Molina-Navarro, J. Org. Chem. 2007, 72, 7462;
- (2007) J. Org. Chem. , vol.72 , pp. 7462
- González, M.A.¹ Molina-Navarro, S.²

13
- 84864426923
- C. Gregg, M. V. Perkins, Org. Biomol. Chem. 2012, 10, 6547;
- (2012) Org. Biomol. Chem. , vol.10 , pp. 6547
- Gregg, C.¹ Perkins, M.V.²

14
- 84879210420
- P. B. Thakur, K. Sirisha, A. V. S. Sarma, J. B. Nanubolu, H. M. Meshram, Tetrahedron 2013, 69, 6415.
- (2013) Tetrahedron , vol.69 , pp. 6415
- Thakur, P.B.¹ Sirisha, K.² Sarma, A.V.S.³ Nanubolu, J.B.⁴ Meshram, H.M.⁵

15
- 0037047534
- M. Palucki, J. M. Um, N. Yasuda, D. A. Conlon, F. R. Tsay, F. W. Hartner, Y. Hsiao, B. Marcue, S. Karady, D. L. Hughes, P. G. Dormer, P. J. Reider, J. Org. Chem. 2002, 67, 5508;
- (2002) J. Org. Chem. , vol.67 , pp. 5508
- Palucki, M.¹ Um, J.M.² Yasuda, N.³ Conlon, D.A.⁴ Tsay, F.R.⁵ Hartner, F.W.⁶ Hsiao, Y.⁷ Marcue, B.⁸ Karady, S.⁹ Hughes, D.L.¹⁰ Dormer, P.G.¹¹ Reider, P.J.¹²

16
- 0000633066
- K. J. Shin, H. R. Moon, C. George, V. E. Marquez, J. Org. Chem. 2000, 65, 2172;
- (2000) J. Org. Chem. , vol.65 , pp. 2172
- Shin, K.J.¹ Moon, H.R.² George, C.³ Marquez, V.E.⁴

17
- 0033709253
- U. Kazmaier, S. Maier, F. L. Zumpe, Synlett 2000, 1523;
- (2000) Synlett , pp. 1523
- Kazmaier, U.¹ Maier, S.² Zumpe, F.L.³

18
- 34250214917
- W. Lin, C. K. Zercher, J. Org. Chem. 2007, 72, 4390.
- (2007) J. Org. Chem. , vol.72 , pp. 4390
- Lin, W.¹ Zercher, C.K.²

19
- 0001556825
- M. F. Carroll, A. R. Bader, J. Am. Chem. Soc. 1953, 75, 5400;
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 5400
- Carroll, M.F.¹ Bader, A.R.²

20
- 0000728075
- J. A. Hyatt, P. L. Feldman, R. J. Clemens, J. Org. Chem. 1984, 49, 5105;
- (1984) J. Org. Chem. , vol.49 , pp. 5105
- Hyatt, J.A.¹ Feldman, P.L.² Clemens, R.J.³

21
- 0000392068
- R. J. Clemens, J. A. Hyatt, J. Org. Chem. 1985, 50, 2431;
- (1985) J. Org. Chem. , vol.50 , pp. 2431
- Clemens, R.J.¹ Hyatt, J.A.²

22
- 0028278565
- M. Sato, S. Sunami, Y. Sugita, C. Kaneko, Chem. Pharm. Bull. 1994, 42, 839;
- (1994) Chem. Pharm. Bull. , vol.42 , pp. 839
- Sato, M.¹ Sunami, S.² Sugita, Y.³ Kaneko, C.⁴

23
- 0001444055
- M. Sato, S. Sunami, Y. Sugita, C. Kaneko, Heterocycles 1995, 41, 1435;
- (1995) Heterocycles , vol.41 , pp. 1435
- Sato, M.¹ Sunami, S.² Sugita, Y.³ Kaneko, C.⁴

24
- 0001151356
- R. A. Singer, E. M. Carreira, J. Am. Chem. Soc. 1995, 117, 12360;
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 12360
- Singer, R.A.¹ Carreira, E.M.²

25
- 0030017687
- D. A. Evans, J. A. Murry, M. C. Kozlowski, J. Am. Chem. Soc. 1996, 118, 5814;
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 5814
- Evans, D.A.¹ Murry, J.A.² Kozlowski, M.C.³

26
- 0038475549
- J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 837
- Krüger, J.¹ Carreira, E.M.²

27
- 33846933027
- G. Helmchen, A. Dahnz, P. Dubon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675;
- (2007) Chem. Commun. , pp. 675
- Helmchen, G.¹ Dahnz, A.² Dubon, P.³ Schelwies, M.⁴ Weihofen, R.⁵

28
- 84891314830
- (Eds.: L. A. Oro, C. Claver), Wiley-VCH, Weinheim
- G. Helmchen, in Iridium Complexes in Organic Synthesis (Eds.:, L. A. Oro, C. Claver,), Wiley-VCH, Weinheim, 2009, p. 211;
- (2009) Iridium Complexes in Organic Synthesis , pp. 211
- Helmchen, G.¹

29
- 78651309468
- J. F. Hartwig, M. J. Pouy, Top. Organomet. Chem. 2011, 34, 169;
- (2011) Top. Organomet. Chem. , vol.34 , pp. 169
- Hartwig, J.F.¹ Pouy, M.J.²

30
- 82055185502
- W.-B. Liu, J.-B. Xia, S.-L. You, Top. Organomet. Chem. 2012, 38, 155;
- (2012) Top. Organomet. Chem. , vol.38 , pp. 155
- Liu, W.-B.¹ Xia, J.-B.² You, S.-L.³

31
- 84859239268
- P. Tosatti, A. Nelson, S. P. Marsden, Org. Biomol. Chem. 2012, 10, 3147.
- (2012) Org. Biomol. Chem. , vol.10 , pp. 3147
- Tosatti, P.¹ Nelson, A.² Marsden, S.P.³

32
- 0030940143
- R. Takeuchi, M. Kashio, Angew. Chem. Int. Ed. Engl. 1997, 36, 263;
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 263
- Takeuchi, R.¹ Kashio, M.²

33
- 0001706269
- Angew. Chem. 1997, 109, 268;
- (1997) Angew. Chem. , vol.109 , pp. 268

34
- 0030771619
- J. P. Janssen, G. Helmchen, Tetrahedron Lett. 1997, 38, 8025;
- (1997) Tetrahedron Lett. , vol.38 , pp. 8025
- Janssen, J.P.¹ Helmchen, G.²

35
- 0037176296
- T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 15164
- Ohmura, T.¹ Hartwig, J.F.²

36
- 0345306320
- C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 14272
- Kiener, C.A.¹ Shu, C.² Incarvito, C.³ Hartwig, J.F.⁴

37
- 0038249086
- T. Kanayama, K. Yoshida, H. Miyabe, Y. Takemoto, Angew. Chem. Int. Ed. 2003, 42, 2054;
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2054
- Kanayama, T.¹ Yoshida, K.² Miyabe, H.³ Takemoto, Y.⁴

38
- 55349112693
- Angew. Chem. 2003, 115, 2100;
- (2003) Angew. Chem. , vol.115 , pp. 2100

39
- 0037353622
- B. Bartels, C. Garcia-Yebra, G. Helmchen, Eur. J. Org. Chem. 2003, 1097;
- (2003) Eur. J. Org. Chem. , pp. 1097
- Bartels, B.¹ Garcia-Yebra, C.² Helmchen, G.³

40
- 33746302230
- M. Schelwies, P. Dübon, G. Helmchen, Angew. Chem. Int. Ed. 2006, 45, 2466;
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 2466
- Schelwies, M.¹ Dübon, P.² Helmchen, G.³

41
- 85028218982
- Angew. Chem. 2006, 118, 2526;
- (2006) Angew. Chem. , vol.118 , pp. 2526

42
- 33645419779
- A. Dahnz, G. Helmchen, Synlett 2006, 697;
- (2006) Synlett , pp. 697
- Dahnz, A.¹ Helmchen, G.²

43
- 33646183971
- D. Polet, A. Alexakis, K. Tissot-Croset, C. Corminboeuf, K. Ditrich, Chem. Eur. J. 2006, 12, 3596;
- (2006) Chem. Eur. J. , vol.12 , pp. 3596
- Polet, D.¹ Alexakis, A.² Tissot-Croset, K.³ Corminboeuf, C.⁴ Ditrich, K.⁵

44
- 58449122728
- D. Polet, X. Rathgeb, C. A. Falciola, J.-B. Langlois, H. S. El, A. Alexakis, Chem. Eur. J. 2009, 15, 1205;
- (2009) Chem. Eur. J. , vol.15 , pp. 1205
- Polet, D.¹ Rathgeb, X.² Falciola, C.A.³ Langlois, J.-B.⁴ El, H.S.⁵ Alexakis, A.⁶

45
- 84863276579
- W.-B. Liu, C. Zheng, C.-X. Zhuo, L.-X. Dai, S.-L. You, J. Am. Chem. Soc. 2012, 134, 4812;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 4812
- Liu, W.-B.¹ Zheng, C.² Zhuo, C.-X.³ Dai, L.-X.⁴ You, S.-L.⁵

46
- 84880784188
- W.-B. Liu, C. M. Reeves, S. C. Virgil, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 10626;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 10626
- Liu, W.-B.¹ Reeves, C.M.² Virgil, S.C.³ Stoltz, B.M.⁴

47
- 84888320099
- W.-B. Liu, C. M. Reeves, S. C. Virgil, B. M. Stoltz, J. Am. Chem. Soc. 2013, 135, 17298;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 17298
- Liu, W.-B.¹ Reeves, C.M.² Virgil, S.C.³ Stoltz, B.M.⁴

48
- 84873661355
- W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2013, 135, 2068;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 2068
- Chen, W.¹ Hartwig, J.F.²

49
- 84892179484
- W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 377.
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 377
- Chen, W.¹ Hartwig, J.F.²

50
- 84866494263
- W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 15249;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 15249
- Chen, W.¹ Hartwig, J.F.²

51
- 84871371865
- M. A. Schafroth, D. Sarlah, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc. 2012, 134, 20276;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 20276
- Schafroth, M.A.¹ Sarlah, D.² Krautwald, S.³ Carreira, E.M.⁴

52
- 84872776762
- J. Y. Hamilton, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2013, 135, 994;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 994
- Hamilton, J.Y.¹ Sarlah, D.² Carreira, E.M.³

53
- 84880109272
- J. Y. Hamilton, D. Sarlah, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 7532;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 7532
- Hamilton, J.Y.¹ Sarlah, D.² Carreira, E.M.³

54
- 84918801460
- Angew. Chem. 2013, 125, 7680;
- (2013) Angew. Chem. , vol.125 , pp. 7680

55
- 84878349078
- S. Krautwald, D. Sarlah, M. A. Schafroth, E. M. Carreira, Science 2013, 340, 1065;
- (2013) Science , vol.340 , pp. 1065
- Krautwald, S.¹ Sarlah, D.² Schafroth, M.A.³ Carreira, E.M.⁴

56
- 84878658105
- C.-X. Zhuo, Q.-F. Wu, Q. Zhao, Q.-L. Xu, S.-L. You, J. Am. Chem. Soc. 2013, 135, 8169;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 8169
- Zhuo, C.-X.¹ Wu, Q.-F.² Zhao, Q.³ Xu, Q.-L.⁴ You, S.-L.⁵

57
- 84896878215
- J. Y. Hamilton, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3006;
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 3006
- Hamilton, J.Y.¹ Sarlah, D.² Carreira, E.M.³

58
- 84896870944
- S. Krautwald, M. A. Schafroth, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2014, 136, 3020;
- (2014) J. Am. Chem. Soc. , vol.136 , pp. 3020
- Krautwald, S.¹ Schafroth, M.A.² Sarlah, D.³ Carreira, E.M.⁴

59
- 84905822679
- M. Chen, J. F. Hartwig, Angew. Chem. Int. Ed. 2014, 53, 8691-8695;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 8691-8695
- Chen, M.¹ Hartwig, J.F.²

60
- 84958226738
- Angew. Chem. 2014, 126, 8835-8839;
- (2014) Angew. Chem. , vol.126 , pp. 8835-8839

61
- 84903158938
- Z.-P. Yang, Q.-F. Wu, S.-L. You, Angew. Chem. Int. Ed. 2014, 53, 6986-6989;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 6986-6989
- Yang, Z.-P.¹ Wu, Q.-F.² You, S.-L.³

62
- 84922020210
- Angew. Chem. 2014, 126, 7106-7109.
- (2014) Angew. Chem. , vol.126 , pp. 7106-7109

63
- 0032557195
- J. Burfeindt, M. Patz, M. Mueller, H. Mayr, J. Am. Chem. Soc. 1998, 120, 3629.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 3629
- Burfeindt, J.¹ Patz, M.² Mueller, M.³ Mayr, H.⁴

64
- 68049115646
- C.-L. Gu, L. Liu, D. Wang, Y.-J. Chen, J. Org. Chem. 2009, 74, 5754;
- (2009) J. Org. Chem. , vol.74 , pp. 5754
- Gu, C.-L.¹ Liu, L.² Wang, D.³ Chen, Y.-J.⁴

65
- 0000577782
- R. W. Dugger, C. H. Heathcock, J. Org. Chem. 1980, 45, 1181;
- (1980) J. Org. Chem. , vol.45 , pp. 1181
- Dugger, R.W.¹ Heathcock, C.H.²

66
- 0001395336
- B. Lei, A. Fallis, Can. J. Chem. 1991, 69, 1450.
- (1991) Can. J. Chem. , vol.69 , pp. 1450
- Lei, B.¹ Fallis, A.²

67
- 84998406097
- M. Sato, N. Kanuma, T. Kato, Chem. Pharm. Bull. 1984, 32, 106;
- (1984) Chem. Pharm. Bull. , vol.32 , pp. 106
- Sato, M.¹ Kanuma, N.² Kato, T.³

68
- 85011124338
- M. Sato, H. Ogasawara, T. Kato, Chem. Pharm. Bull. 1984, 32, 2602;
- (1984) Chem. Pharm. Bull. , vol.32 , pp. 2602
- Sato, M.¹ Ogasawara, H.² Kato, T.³

69
- 0027205475
- F. G. West, P. V. Fisher, G. U. Gunawardena, S. Mitchellt, Tetrahedron Lett. 1993, 34, 4583;
- (1993) Tetrahedron Lett. , vol.34 , pp. 4583
- West, F.G.¹ Fisher, P.V.² Gunawardena, G.U.³ Mitchellt, S.⁴

70
- 31944450141
- A. C. Hart, A. J. Phillips, J. Am. Chem. Soc. 2006, 128, 1094;
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1094
- Hart, A.C.¹ Phillips, A.J.²

71
- 33644962973
- M. T. Crimmins, A. C. Smith, Org. Lett. 2006, 8, 1003;
- (2006) Org. Lett. , vol.8 , pp. 1003
- Crimmins, M.T.¹ Smith, A.C.²

72
- 38349186964
- D. W. Custar, T. P. Zabawa, K. A. Scheidt, J. Am. Chem. Soc. 2008, 130, 804;
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 804
- Custar, D.W.¹ Zabawa, T.P.² Scheidt, K.A.³

73
- 78049498801
- T. Hoye, M. E. Danielson, A. E. May, H. Zhao, J. Org. Chem. 2010, 75, 7052;
- (2010) J. Org. Chem. , vol.75 , pp. 7052
- Hoye, T.¹ Danielson, M.E.² May, A.E.³ Zhao, H.⁴

74
- 84888133628
- I. Yavari, M. J. Bayat, S. Skoulika, Synlett 2013, 2591.
- (2013) Synlett , pp. 2591
- Yavari, I.¹ Bayat, M.J.² Skoulika, S.³

75
- 0001246453
- B. J. L. Royles, Chem. Rev. 1995, 95, 1981.
- (1995) Chem. Rev. , vol.95 , pp. 1981
- Royles, B.J.L.¹

76
- 85066391346
- CCDC 1023607 (5 j) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC 1023607 (5 j) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.

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