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Angewandte Chemie - International Edition

Volumn 47, Issue 5, 2008, Pages 894-897

Exploiting self-assembly for ligand-scaffold optimization: Substrate-tailored ligands for efficient catalytic asymmetric hydroboration

(2) Moteki, Shin A a Takacs, James M a

a UNIVERSITY OF NEBRASKA LINCOLN (United States)

Author keywords

Asymmetric synthesis; Combinatorial chemistry; Hydroboration; Self assembly; Stereoselective catalysis

Indexed keywords

CATALYSIS; DERIVATIVES; ENANTIOSELECTIVITY; SELF ASSEMBLY; STYRENE;

ASYMMETRIC SYNTHESIS; COMBINATORIAL CHEMISTRY; HYDROBORATION;

LIGANDS;

ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; BORANE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; RHODIUM; STYRENE DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; BENZENE DERIVATIVES; BORANES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM; STYRENES; ZINC;

EID: 38549107599 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200703127 Document Type: Article

Times cited : (73)

References (45)

1
- 0000608693
- D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855;
- (1985) Angew. Chem , vol.97 , pp. 854-855
- Männig, D.¹ Nöth, H.²

2
- 84985609802
- Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879.
- (1985) Angew. Chem. Int. Ed. Engl , vol.24 , pp. 878-879

3
- 18244395541
- Recent reviews: a
- Recent reviews: a) A.-M. Carroll, T. P. O'Sullivan, P. J. Guiry, Adv. Synth. Catal. 2005, 347, 609-631;
- (2005) Adv. Synth. Catal , vol.347 , pp. 609-631
- Carroll, A.-M.¹ O'Sullivan, T.P.² Guiry, P.J.³

4
- 17644381216
- b) C. M. Vogels, S. A. Westcott, Curr. Org. Chem. 2005, 9, 687-699;
- (2005) Curr. Org. Chem , vol.9 , pp. 687-699
- Vogels, C.M.¹ Westcott, S.A.²

5
- 2542451759
- c) P. J. Guiry, C. P. Saunders, Adv. Synth. Catal. 2004, 346, 497-537;
- (2004) Adv. Synth. Catal , vol.346 , pp. 497-537
- Guiry, P.J.¹ Saunders, C.P.²

6
- 0347992911
- d) C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695-4712.
- (2003) Eur. J. Org. Chem , pp. 4695-4712
- Crudden, C.M.¹ Edwards, D.²

7
- 33746660714
- a) S. A. Moteki, D. Wu, K. L. Chandra, D. S. Reddy, J. M. Takacs, Org. Lett. 2006, 8, 3097-3100;
- (2006) Org. Lett , vol.8 , pp. 3097-3100
- Moteki, S.A.¹ Wu, D.² Chandra, K.L.³ Reddy, D.S.⁴ Takacs, J.M.⁵

8
- 0037012827
- b) F. Y. Kwong, Q. Yang, T. C. W. Mak, A. S. C. Chan, K. S. Chan, J. Org. Chem. 2002, 67, 2769-2777;
- (2002) J. Org. Chem , vol.67 , pp. 2769-2777
- Kwong, F.Y.¹ Yang, Q.² Mak, T.C.W.³ Chan, A.S.C.⁴ Chan, K.S.⁵

9
- 0035684391
- c) C. Köllner, A. Togni, Can. J. Chem. 2001, 79, 1762-1774;
- (2001) Can. J. Chem , vol.79 , pp. 1762-1774
- Köllner, C.¹ Togni, A.²

10
- 0001372013
- d) A. Schnyder, L. Hintermann, A. Togni, Angew. Chem. 1995, 107, 996-998;
- (1995) Angew. Chem , vol.107 , pp. 996-998
- Schnyder, A.¹ Hintermann, L.² Togni, A.³

11
- 33748511263
- Angew. Chem. Int. Ed. Engl. 1995, 34, 931-933;
- (1995) Angew. Chem. Int. Ed. Engl , vol.34 , pp. 931-933

12
- 0000345787
- e) A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijani, J. Am. Chem. Soc. 1994, 116, 4062-4066.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 4062-4066
- Togni, A.¹ Breutel, C.² Schnyder, A.³ Spindler, F.⁴ Landert, H.⁵ Tijani, A.⁶

13
- 0032944239
- a) H. Doucet, E. Fernandez, T. P. Layzell, J. M. Brown, Chem. Eur. J. 1999, 5, 1320-1330;
- (1999) Chem. Eur. J , vol.5 , pp. 1320-1330
- Doucet, H.¹ Fernandez, E.² Layzell, T.P.³ Brown, J.M.⁴

14
- 33845183513
- b) T. Hayashi, Y. Matsumoto, Y. Ito, J. Am. Chem. Soc. 1989, 111, 3426-3428;
- (1989) J. Am. Chem. Soc , vol.111 , pp. 3426-3428
- Hayashi, T.¹ Matsumoto, Y.² Ito, Y.³

15
- 0025851101
- c) T. Hayashi, Y. Matsumoto, Y. Ito, Tetrahedron: Asymmetry 1991, 2, 601-612.
- (1991) Tetrahedron: Asymmetry , vol.2 , pp. 601-612
- Hayashi, T.¹ Matsumoto, Y.² Ito, Y.³

16
- 33745713813
- For reviews highlighting recent strategies, see, a
- For reviews highlighting recent strategies, see : a) S. J. Reyes, K. Burgess, Chem. Soc. Rev. 2006, 35, 416-423;
- (2006) Chem. Soc. Rev , vol.35 , pp. 416-423
- Reyes, S.J.¹ Burgess, K.²

17
- 33745826329
- b) A. J. Sandee, J. N. H. Reek, Dalton Trans. 2006, 3385-3391;
- (2006) Dalton Trans , pp. 3385-3391
- Sandee, A.J.¹ Reek, J.N.H.²

18
- 33746300381
- c) B. Breit, Angew. Chem. 2005, 117, 6976-6986;
- (2005) Angew. Chem , vol.117 , pp. 6976-6986
- Breit, B.¹

19
- 27544471835
- Angew. Chem. Int. Ed. 2005, 44, 6816-6825;
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6816-6825

20
- 22844452201
- d) M. J. Wilkinson, P. W. N. M. van Leeuwen, J. N. H. Reek, Org. Biomol. Chem. 2005, 3, 2371-2383.
- (2005) Org. Biomol. Chem , vol.3 , pp. 2371-2383
- Wilkinson, M.J.¹ van Leeuwen, P.W.N.M.² Reek, J.N.H.³

21
- 38549128111
- For more recent examples, see: a
- For more recent examples, see: a) C. Machut, J. Patrigeon, S. Tilloy, H. Bricout, F. Hapiot, E. Monflier, Angew. Chem. 2007, 119, 3100-3102;
- (2007) Angew. Chem , vol.119 , pp. 3100-3102
- Machut, C.¹ Patrigeon, J.² Tilloy, S.³ Bricout, H.⁴ Hapiot, F.⁵ Monflier, E.⁶

22
- 34250890138
- Angew. Chem. Int. Ed. 2007, 46, 3040-3042;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 3040-3042

23
- 33847163177
- b) S. Chikkali, D. Gudat, M. Niemeyer, Chem. Commun. 2007, 981-983;
- (2007) Chem. Commun , pp. 981-983
- Chikkali, S.¹ Gudat, D.² Niemeyer, M.³

24
- 33847082418
- c) A. J. Sandee, A. M. Van der Burg, J. N. H. Reek, Chem. Commun. 2007, 864-866;
- (2007) Chem. Commun , pp. 864-866
- Sandee, A.J.¹ Van der Burg, A.M.² Reek, J.N.H.³

25
- 38049068524
- d) M. L. Clarke, J. A. Fuentes, Angew. Chem. 2007, 119, 948-951;
- (2007) Angew. Chem , vol.119 , pp. 948-951
- Clarke, M.L.¹ Fuentes, J.A.²

26
- 33846684924
- Angew. Chem. Int. Ed. 2007, 46, 930-933;
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 930-933

27
- 33751107949
- e) M. Kuil, P. E. Goudriaan, P. W. N. M. Van Leeuwen, J. N. H. Reek, Chem. Commun. 2006, 4679-4681;
- (2006) Chem. Commun , pp. 4679-4681
- Kuil, M.¹ Goudriaan, P.E.² Van Leeuwen, P.W.N.M.³ Reek, J.N.H.⁴

28
- 33750698607
- f) Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14212-14213;
- (2006) J. Am. Chem. Soc , vol.128 , pp. 14212-14213
- Liu, Y.¹ Sandoval, C.A.² Yamaguchi, Y.³ Zhang, X.⁴ Wang, Z.⁵ Kato, K.⁶ Ding, K.⁷

29
- 33646743586
- g) S. Jonsson, F. G. J. Odille, P.-O. Norrby, K. Wärnmark, Org. Biomol. Chem. 2006, 4, 1927-1948;
- (2006) Org. Biomol. Chem , vol.4 , pp. 1927-1948
- Jonsson, S.¹ Odille, F.G.J.² Norrby, P.-O.³ Wärnmark, K.⁴

30
- 33846660799
- h) F. Chevallier, B. Breit, Angew. Chem. 2006, 118, 1629-1632;
- (2006) Angew. Chem , vol.118 , pp. 1629-1632
- Chevallier, F.¹ Breit, B.²

31
- 33746303551
- Angew. Chem. Int. Ed. 2006, 45, 1599-1602;
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1599-1602

32
- 33645473788
- i) M. Weis, C. Waloch, W. Seiche, B. Breit, J. Am. Chem. Soc. 2006, 128, 4188-4189;
- (2006) J. Am. Chem. Soc , vol.128 , pp. 4188-4189
- Weis, M.¹ Waloch, C.² Seiche, W.³ Breit, B.⁴

33
- 34250330702
- j) X.-B. Jiang, L. Lefort, P. E. Goudriaan, A. H. M. de Vries, P. W. N. M. van Leeuwen, J. G. de Vries, J. N. H. Reek, Angew. Chem. 2006, 118, 1245-1249;
- (2006) Angew. Chem , vol.118 , pp. 1245-1249
- Jiang, X.-B.¹ Lefort, L.² Goudriaan, P.E.³ de Vries, A.H.M.⁴ van Leeuwen, P.W.N.M.⁵ de Vries, J.G.⁶ Reek, J.N.H.⁷

34
- 33745814238
- Angew. Chem. Int. Ed. 2006, 45, 1223-1227.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 1223-1227

35
- 1842637842
- a) J. M. Takacs, D. S. Reddy, S. A. Moteki, D. Wu, H. Palencia, J. Am. Chem. Soc. 2004, 126, 4494-4495;
- (2004) J. Am. Chem. Soc , vol.126 , pp. 4494-4495
- Takacs, J.M.¹ Reddy, D.S.² Moteki, S.A.³ Wu, D.⁴ Palencia, H.⁵

36
- 33644553779
- b) J. M. Takacs, K. Chaiseeda, S. A. Moteki, D. S. Reddy, D. Wu, K. Chandra, Pure Appl. Chem. 2006, 78, 501-509.
- (2006) Pure Appl. Chem , vol.78 , pp. 501-509
- Takacs, J.M.¹ Chaiseeda, K.² Moteki, S.A.³ Reddy, D.S.⁴ Wu, D.⁵ Chandra, K.⁶

37
- 77956672958
- J. Sakaki, W. B. Schweizer, D. Seebach, Helv. Chim. Acta 1993, 76, 2654-2665.
- (1993) Helv. Chim. Acta , vol.76 , pp. 2654-2665
- Sakaki, J.¹ Schweizer, W.B.² Seebach, D.³

38
- 14644424689
- a) J. M. Takacs, P. M. Hrvatin, J. M. Atkins, D. S. Reddy, J. L. Clark, New J. Chem. 2005, 29, 263-265;
- (2005) New J. Chem , vol.29 , pp. 263-265
- Takacs, J.M.¹ Hrvatin, P.M.² Atkins, J.M.³ Reddy, D.S.⁴ Clark, J.L.⁵

39
- 33746119199
- b) J. M. Atkins, S. A. Moteki, S. G. DiMagno, J. M. Takacs, Org. Lett. 2006, 8, 2759-2762.
- (2006) Org. Lett , vol.8 , pp. 2759-2762
- Atkins, J.M.¹ Moteki, S.A.² DiMagno, S.G.³ Takacs, J.M.⁴

40
- 38549089965
- P.Rh = 250 Hz).
- P.Rh = 250 Hz).

41
- 38549180942
- In contrast to the results found using pinacol borane, the use of catechol borane gave low levels of asymmetric induction
- In contrast to the results found using pinacol borane, the use of catechol borane gave low levels of asymmetric induction.

42
- 38549093975
- The regioselectivity also varies as a function of SAL scaffold structure, but to a lesser extent 70-99% α-3, with {RhIBF 4} catalysts generally affording higher regioselectivity. We find no strong correlation between regio- and enantioselectivity, however, there seems to be a loose correlation between enantioselectivity and conversion/yield under the conditions examined
- 4} catalysts generally affording higher regioselectivity. We find no strong correlation between regio- and enantioselectivity, however, there seems to be a loose correlation between enantioselectivity and conversion/yield under the conditions examined.

43
- 10944265440
- and references therein
- A. M. Segarra, E. Daura-Oller, C. Claver, J. M. Poblet, C. Bo, E. Fernandez, Chem. Eur. J. 2004, 10, 6456-6467, and references therein.
- (2004) Chem. Eur. J , vol.10 , pp. 6456-6467
- Segarra, A.M.¹ Daura-Oller, E.² Claver, C.³ Poblet, J.M.⁴ Bo, C.⁵ Fernandez, E.⁶

44
- 1842638570
- and references therein
- E. Daura-Oller, A. M. Segarra, J. M. Poblet, C. Claver, E. Fernandez, C. Bo, J. Org. Chem. 2004, 69, 2669-2680, and references therein.
- (2004) J. Org. Chem , vol.69 , pp. 2669-2680
- Daura-Oller, E.¹ Segarra, A.M.² Poblet, J.M.³ Claver, C.⁴ Fernandez, E.⁵ Bo, C.⁶

45
- 38549101031
- 2OTf] using (SS,RR)-SAL CH.
- 2OTf] using (SS,RR)-SAL CH.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.