SCOPUS 정보 검색 플랫폼

Chemical Communications

Volumn , Issue 39, 2006, Pages 4093-4095

Enantioselective rhodium-catalyzed addition of arylboronic acids to trifluoromethyl ketones

(5) Martina, Sébastien L X a Jagt, Richard B C a De Vries, Johannes G b Feringa, Ben L a Minnaard, Adriaan J a

a UNIVERSITY OF GRONINGEN (Netherlands)

b DSM Pharmaceutical Products (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2,2,2 TRIFLUOROACETOPHENONE; ACETOPHENONE DERIVATIVE; BORONIC ACID DERIVATIVE; KETONE DERIVATIVE; PHOSPHORAMIDOUS ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; TRIFLUOROMETHYLKETONE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 33749523245 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b609453h Document Type: Article

Times cited : (77)

References (68)

1
- 33748053657
- A. M. Thayer Chem. Eng. News 2006 84 15
- (2006) Chem. Eng. News , vol.84 , pp. 15
- Thayer, A.M.¹

2
- 0034926661
- B. E. Smart J. Fluorine Chem. 2001 109 3
- (2001) J. Fluorine Chem. , vol.109 , pp. 3
- Smart, B.E.¹

3
- 0003508266
- T. Hiyama, Springer, New York
- Organofluorine compounds. Chemistry and Applications, ed., T. Hiyama, Springer, New York, 2000
- (2000) Organofluorine Compounds. Chemistry and Applications, Ed.

4
- 0003518240
- I. Ojima, J. R. McCarthy and J. T. Welch, ACS Editions, Washington DC
- Biomedical Frontiers of Fluorine Chemistry, ed., I. Ojima,, J. R. McCarthy, and, J. T. Welch, ACS Editions, Washington DC, 1996
- (1996) Biomedical Frontiers of Fluorine Chemistry, Ed.

5
- 0003461236
- A. Becker, Eyrolles, Paris
- Inventory of Industrial Fluoro-Biochemicals, ed., A. Becker, Eyrolles, Paris, 1996
- (1996) Inventory of Industrial Fluoro-Biochemicals, Ed.

6
- 0003536898
- R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York
- Organofluorine Chemistry, Principles and Commercial Applications, ed., R. E. Banks,, B. E. Smart, and, J. C. Tatlow, Plenum Press, New York, 1994
- (1994) Organofluorine Chemistry, Principles and Commercial Applications, Ed.

7
- 0003490830
- R. Filler, Y. Kobayashi and L. N. Yagupolskii, Elsevier, Amsterdam
- Organofluorine Compounds in Medicinal and Biomedical Applications, ed., R. Filler,, Y. Kobayashi, and, L. N. Yagupolskii, Elsevier, Amsterdam, 1993
- (1993) Organofluorine Compounds in Medicinal and Biomedical Applications, Ed.

8
- 0003907264
- J. T. Welch and S. Eswarakrishnan, Wiley, New York
- Fluorine in Bioorganic Chemistry, ed., J. T. Welch, and, S. Eswarakrishnan, Wiley, New York, 1991
- (1991) Fluorine in Bioorganic Chemistry, Ed.

9
- 0003610755
- J. F. Liebman, A. Greenberg and W. R. Dolbier, Jr., VCH, New York
- Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Applications, ed., J. F. Liebman,, A. Greenberg, and, W. R. Dolbier, Jr., VCH, New York, 1988
- (1988) Fluorine-Containing Molecules. Structure, Reactivity, Synthesis, and Applications, Ed.

10
- 0002261716
- H. Schofield J. Fluorine Chem. 1999 100 7
- (1999) J. Fluorine Chem. , vol.100 , pp. 7
- Schofield, H.¹

11
- 1542534457
- J. A. Wilkinson Chem. Rev. 1992 92 505
- (1992) Chem. Rev. , vol.92 , pp. 505
- Wilkinson, J.A.¹

12
- 0025649186
- For some examples of pharmacophores containing a trifluoromethyl group, see:
- D. Seebach Angew. Chem., Int. Ed. Engl. 1990 29 1320
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 1320
- Seebach, D.¹

13
- 0347753811
- B. Jiang Y.-G. Si Angew. Chem., Int. Ed. 2004 43 216
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 216
- Jiang, B.¹ Si, Y.-G.²

14
- 0034097996
- L. M. Jackson C. J. Hawkey Drugs 2000 59 1207
- (2000) Drugs , vol.59 , pp. 1207
- Jackson, L.M.¹ Hawkey, C.J.²

15
- 0000377939
- M. L. P. Price W. J. Jorgensen J. Am. Chem. Soc. 2000 122 9455
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9455
- Price, M.L.P.¹ Jorgensen, W.J.²

16
- 0033105506
- L. Tan C.-Y. Chen R. D. Tillyer E. J. J. Grabowski P. J. Reider Angew. Chem., Int. Ed. 1999 38 711
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 711
- Tan, L.¹ Chen, C.-Y.² Tillyer, R.D.³ Grabowski, E.J.J.⁴ Reider, P.J.⁵

17
- 0034669286
- For a selection of recent examples of trifluoromethylation of carbonyl compounds, see:
- F. Xu R. A. Reamer R. D. Tillyer J. M. Cummins E. J. J. Grabowski P. J. Reider D. B. Collum J. C. Huffman J. Am. Chem. Soc. 2000 122 11212
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 11212
- Xu, F.¹ Reamer, R.A.² Tillyer, R.D.³ Cummins, J.M.⁴ Grabowski, E.J.J.⁵ Reider, P.J.⁶ Collum, D.B.⁷ Huffman, J.C.⁸

18
- 17044408332
- Y. Chang C. Cai Tetrahedron Lett. 2005 46 3161
- (2005) Tetrahedron Lett. , vol.46 , pp. 3161
- Chang, Y.¹ Cai, C.²

19
- 13244292263
- S. Roussel T. Billard B. R. Langlois L. Saint-Jalmes Chem. Eur. J. 2005 11 939
- (2005) Chem. Eur. J. , vol.11 , pp. 939
- Roussel, S.¹ Billard, T.² Langlois, B.R.³ Saint-Jalmes, L.⁴

20
- 0038441453
- G. K. S. Prakash J. Hu G. A. Olah J. Org. Chem. 2003 68 4457
- (2003) J. Org. Chem. , vol.68 , pp. 4457
- Prakash, G.K.S.¹ Hu, J.² Olah, G.A.³

21
- 0037280952
- B. R. Langlois T. Billard Synthesis 2003 185
- (2003) Synthesis , pp. 185
- Langlois, B.R.¹ Billard, T.²

22
- 0041309557
- J. Joubert S. Roussel C. Christophe T. Billard B. R. Langlois T. Vidal Angew. Chem., Int. Ed. 2003 42 3133
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3133
- Joubert, J.¹ Roussel, S.² Christophe, C.³ Billard, T.⁴ Langlois, B.R.⁵ Vidal, T.⁶

23
- 0141856281
- G. K. S. Prakash J. Hu G. A. Olah Org. Lett. 2003 5 3253
- (2003) Org. Lett. , vol.5 , pp. 3253
- Prakash, G.K.S.¹ Hu, J.² Olah, G.A.³

24
- 5644248361
- For a recent review on nucleophilic trifluoromethylation reagents and their stereoselective aspects, see:
- S. Roussel T. Billard B. R. Langlois L. Saint-Jalmes Synthesis 2004 2119
- (2004) Synthesis , pp. 2119
- Roussel, S.¹ Billard, T.² Langlois, B.R.³ Saint-Jalmes, L.⁴

25
- 17644427052
- For reviews on the formation of quaternary carbon centers, see:
- B. R. Langlois T. Billard S. Roussel J. Fluorine Chem. 2005 126 173
- (2005) J. Fluorine Chem. , vol.126 , pp. 173
- Langlois, B.R.¹ Billard, T.² Roussel, S.³

26
- 27544469612
- J. Christoffers and A. Baro, Wiley-VCH, Weinheim
- Quaternary Stereocenters. Challenges and Solutions for Organic Synthesis, ed., J. Christoffers, and, A. Baro, Wiley-VCH, Weinheim, 2005
- (2005) Quaternary Stereocenters. Challenges and Solutions for Organic Synthesis, Ed.

27
- 32644439884
- B. M. Trost C. Jiang Synthesis 2006 369
- (2006) Synthesis , pp. 369
- Trost, B.M.¹ Jiang, C.²

28
- 27544458968
- J. Christoffers A. Baro Adv. Synth. Catal. 2005 247 1473
- (2005) Adv. Synth. Catal. , vol.247 , pp. 1473
- Christoffers, J.¹ Baro, A.²

29
- 0346639268
- D. J. Ramón M. Yus Curr. Org. Chem. 2004 8 149
- (2004) Curr. Org. Chem. , vol.8 , pp. 149
- Ramón, D.J.¹ Yus, M.²

30
- 0344064789
- I. Denissova L. Barriault Tetrahedron 2003 59 10105
- (2003) Tetrahedron , vol.59 , pp. 10105
- Denissova, I.¹ Barriault, L.²

31
- 0032473509
- For an enantioselective indium-mediated allylation reaction on trifluoromethyl ketones, see:
- E. J. Corey A. Guzman-Perez Angew. Chem., Int. Ed. 1998 37 388
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 388
- Corey, E.J.¹ Guzman-Perez, A.²

32
- 0033601395
- for a diastereoselective methyl Grignard addition to trifluoromethyl ketone, see:
- T.-P. Loh J.-R. Zhou X.-R. Li Tetrahedron Lett. 1999 40 9333
- (1999) Tetrahedron Lett. , vol.40 , pp. 9333
- Loh, T.-P.¹ Zhou, J.-R.² Li, X.-R.³

33
- 4544235069
- for the enantioselective alkynylation of trifluoromethyl ketoaniline using metal alkynylides with a stoichiometric amount of chiral mediator, see:
- J. M. Andrés R. Pedrosa A. Pérez-Encabo Eur. J. Org. Chem. 2004 1558
- (2004) Eur. J. Org. Chem. , pp. 1558
- Andrés, J.M.¹ Pedrosa, R.² Pérez-Encabo, A.³

34
- 0037090085
- B. Jiang Y. Feng Tetrahedron Lett. 2002 43 2975
- (2002) Tetrahedron Lett. , vol.43 , pp. 2975
- Jiang, B.¹ Feng, Y.²

35
- 0000377939
- M. L. P. Price W. J. Jorgensen J. Am. Chem. Soc. 2000 122 9455
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9455
- Price, M.L.P.¹ Jorgensen, W.J.²

36
- 0033105506
- For a review on the enantioselective addition of zinc reagents to ketones, see:
- L. Tan C.-Y. Chen R. D. Tillyer W. J. J. Grabowski P. J. Reider Angew. Chem., Int. Ed. 1999 38 711
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 711
- Tan, L.¹ Chen, C.-Y.² Tillyer, R.D.³ Grabowski, W.J.J.⁴ Reider, P.J.⁵

37
- 0347131100
- for the first example of the catalytic enantioselective addition of diphenylzinc to ketones, see:
- D. J. Ramón M. Yus Angew. Chem., Int. Ed. 2004 43 284
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 284
- Ramón, D.J.¹ Yus, M.²

38
- 0032554099
- for some recent examples of the enantioselective addition of zinc reagents to ketones, see:
- P. I. Dosa G. C. Fu J. Am. Chem. Soc. 1998 120 445
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 445
- Dosa, P.I.¹ Fu, G.C.²

39
- 20444484058
- H. Li P. J. Walsh J. Am. Chem. Soc. 2005 127 8355
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8355
- Li, H.¹ Walsh, P.J.²

40
- 28544452446
- S.-J. Jeon H. Li P. J. Walsh J. Am. Chem. Soc. 2005 127 16416
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 16416
- Jeon, S.-J.¹ Li, H.² Walsh, P.J.³

41
- 33749509163
- P. G. Cozzi J. Rudolph C. Bolm P.-O. Norrby C. Tomasisni J. Org. Chem. 2005 16 3341
- (2005) J. Org. Chem. , vol.16 , pp. 3341
- Cozzi, P.G.¹ Rudolph, J.² Bolm, C.³ Norrby, P.-O.⁴ Tomasisni, C.⁵

42
- 27544483565
- M. Ni R. Wang Z.-J. Han B. Mao C.-S. Da L. Liu C. Chen Adv. Synth. Catal. 2005 347 1659
- (2005) Adv. Synth. Catal. , vol.347 , pp. 1659
- Ni, M.¹ Wang, R.² Han, Z.-J.³ Mao, B.⁴ Da, C.-S.⁵ Liu, L.⁶ Chen, C.⁷

43
- 1842631438
- H. Li C. García P. J. Walsh Proc. Natl. Acad. Sci. USA 2004 5425
- (2004) Proc. Natl. Acad. Sci. USA , pp. 5425
- Li, H.¹ García, C.² Walsh, P.J.³

44
- 12344275269
- S.-J. Jeon H. Li C. García L. K. LaRochelle P. J. Walsh J. Org. Chem. 2005 70 448
- (2005) J. Org. Chem. , vol.70 , pp. 448
- Jeon, S.-J.¹ Li, H.² García, C.³ Larochelle, L.K.⁴ Walsh, P.J.⁵

45
- 0038711344
- P. G. Cozzi Angew. Chem., Int. Ed. 2003 42 2895
- (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 2895
- Cozzi, P.G.¹

46
- 0142074832
- for the enantioselective addition of a vinylsilane reagent to an activated ketone, see:
- C. García P. J. Walsh Org. Lett. 2003 5 3641
- (2003) Org. Lett. , vol.5 , pp. 3641
- García, C.¹ Walsh, P.J.²

47
- 16244383506
- For a review on catalytic asymmetric approaches toward enantiomerically enriched diarylmethanols and diarylmethylamines, see:
- D. Tomioka R. Wada M. Kanai M. Shibasaki J. Am. Chem. Soc. 2005 127 4138
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4138
- Tomioka, D.¹ Wada, R.² Kanai, M.³ Shibasaki, M.⁴

48
- 33745760081
- F. Schmidt R. T. Stemmler J. Rudolph C. Bolm Chem. Soc. Rev. 2006 35 454
- (2006) Chem. Soc. Rev. , vol.35 , pp. 454
- Schmidt, F.¹ Stemmler, R.T.² Rudolph, J.³ Bolm, C.⁴

49
- 2042507954
- N. Miyaura A. Suzuki Chem. Rev. 1995 95 2457
- (1995) Chem. Rev. , vol.95 , pp. 2457
- Miyaura, N.¹ Suzuki, A.²

50
- 84889494843
- D. G. Hall, Wiley-VCH, Weinheim
- Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine, ed., D. G. Hall, Wiley-VCH, Weinheim, 2005
- (2005) Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine, Ed.

51
- 0034975355
- T. Hayashi Synlett 2001 879
- (2001) Synlett , pp. 879
- Hayashi, T.¹

52
- 33746186702
- T. Hayashi K. Yamasaki Chem. Rev. 2003 103 169
- (2003) Chem. Rev. , vol.103 , pp. 169
- Hayashi, T.¹ Yamasaki, K.²

53
- 77955911241
- P. A. Evans, Wiley-VCH Verlag, Weinheim
- Modern Rhodium-Catalyzed Organic Reactions, ed., P. A. Evans, Wiley-VCH Verlag, Weinheim, 2005
- (2005) Modern Rhodium-Catalyzed Organic Reactions, Ed.

54
- 0038251459
- also see:
- J.-G. Boiteau R. Imbos A. J. Minnaard B. L. Feringa Org. Lett. 2003 5 681
- (2003) Org. Lett. , vol.5 , pp. 681
- Boiteau, J.-G.¹ Imbos, R.² Minnaard, A.J.³ Feringa, B.L.⁴

55
- 20544466863
- 1385
- Org. Lett., 2003, 5, 1385
- (2003) Org. Lett. , vol.5

56
- 0345254924
- J.-G. Boiteau A. J. Minnaard B. L. Feringa J. Org. Chem. 2003 68 9481
- (2003) J. Org. Chem. , vol.68 , pp. 9481
- Boiteau, J.-G.¹ Minnaard, A.J.² Feringa, B.L.³

57
- 0141631827
- A. Duursma R. Hoen J. Schuppan R. Hulst A. J. Minnaard B. L. Feringa Org. Lett. 2003 5 3111
- (2003) Org. Lett. , vol.5 , pp. 3111
- Duursma, A.¹ Hoen, R.² Schuppan, J.³ Hulst, R.⁴ Minnaard, A.J.⁵ Feringa, B.L.⁶

58
- 20544440852
- R. B. C. Jagt J. G. de Vries B. L. Feringa A. J. Minnaard Org. Lett. 2005 7 2433
- (2005) Org. Lett. , vol.7 , pp. 2433
- Jagt, R.B.C.¹ De Vries, J.G.² Feringa, B.L.³ Minnaard, A.J.⁴

59
- 0033935279
- B. L. Feringa Acc. Chem. Res. 2000 33 346
- (2000) Acc. Chem. Res. , vol.33 , pp. 346
- Feringa, B.L.¹

60
- 13244251142
- H. Bernsmann M. van den Berg R. Hoen A. J. Minnaard G. Mehler M. T. Reetz J. G. de Vries B. L. Feringa J. Org. Chem. 2005 70 943
- (2005) J. Org. Chem. , vol.70 , pp. 943
- Bernsmann, H.¹ Van Den Berg, M.² Hoen, R.³ Minnaard, A.J.⁴ Mehler, G.⁵ Reetz, M.T.⁶ De Vries, J.G.⁷ Feringa, B.L.⁸

61
- 2942599460
- L. Lefort J. A. F. Boogers A. H. M. de Vries J. G. de Vries Org. Lett. 2004 6 1733
- (2004) Org. Lett. , vol.6 , pp. 1733
- Lefort, L.¹ Boogers, J.A.F.² De Vries, A.H.M.³ De Vries, J.G.⁴

62
- 3042789542
- A. Duursma L. Lefort J. A. F. Boogers A. H. M. de Vries J. G. de Vries A. J. Minnaard B. L. Feringa Org. Biomol. Chem. 2004 2 1682
- (2004) Org. Biomol. Chem. , vol.2 , pp. 1682
- Duursma, A.¹ Lefort, L.² Boogers, J.A.F.³ De Vries, A.H.M.⁴ De Vries, J.G.⁵ Minnaard, A.J.⁶ Feringa, B.L.⁷

63
- 33745577878
- R. B. C. Jagt P. Y. Toullec D. Geerdink J. G. de Vries B. L. Feringa A. J. Minnaard Angew. Chem., Int. Ed. 2006 45 2789
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 2789
- Jagt, R.B.C.¹ Toullec, P.Y.² Geerdink, D.³ De Vries, J.G.⁴ Feringa, B.L.⁵ Minnaard, A.J.⁶

64
- 33344469112
- R. B. C. Jagt P. Y. Toullec J. G. de Vries B. L. Feringa A. J. Minnaard Org. Biomol. Chem. 2006 4 773
- (2006) Org. Biomol. Chem. , vol.4 , pp. 773
- Jagt, R.B.C.¹ Toullec, P.Y.² De Vries, J.G.³ Feringa, B.L.⁴ Minnaard, A.J.⁵

65
- 33746112742
- R. Shintani M. Inoue T. Hayashi Angew. Chem., Int. Ed. 2006 45 3353
- (2006) Angew. Chem., Int. Ed. , vol.45 , pp. 3353
- Shintani, R.¹ Inoue, M.² Hayashi, T.³

66
- 33746147475
- P. Y. Toullec R. B. C. Jagt J. G. de Vries B. L. Feringa A. J. Minnaard Org. Lett. 2006 8 2715
- (2006) Org. Lett. , vol.8 , pp. 2715
- Toullec, P.Y.¹ Jagt, R.B.C.² De Vries, J.G.³ Feringa, B.L.⁴ Minnaard, A.J.⁵

67
- 0032542313
- M. Sakai M. Ueda N. Miyaura Angew. Chem., Int. Ed. 1998 37 3279
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3279
- Sakai, M.¹ Ueda, M.² Miyaura, N.³

68
- 0035944181
- C. Moreau C. Hague A. S. Weller C. G. Frost Tetrahedron Lett. 2001 42 6957
- (2001) Tetrahedron Lett. , vol.42 , pp. 6957
- Moreau, C.¹ Hague, C.² Weller, A.S.³ Frost, C.G.⁴

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