(R)-1,1′-binaphthyl-2-bis(pentafluorophenyl)Borane Lewis acids

Synlett

Volumn , Issue 13, 2004, Pages 2429-2433

  Morrison, Darryl J ^a   Piers, Warren E ^a   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

Allylations; Asymmetric catalysis; Asymmetric synthesis; Boron; Lewis acids

Indexed keywords

ALLYL ALCOHOL; ANISALDEHYDE; BENZENE DERIVATIVE; BORANE DERIVATIVE; FLUORINE DERIVATIVE; LEWIS ACID; NAPHTHYL GROUP;

ALLYLSTANNATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; QUANTUM YIELD; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 8744305036     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832824     Document Type: Article

References (30)

1. (a) For a review on modified BINOL ligands: Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
2. (b) For a series of reviews on chiral Lewis acids in these and other applications see: Comprehensive Asymmetric Catalysis, Vol 1-3; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999.
3. Oh, T.; Lopez, P.; Reilly, M. Eur. J. Org. Chem. 2000, 2901.
4. Hoshi, T.; Shionoiri, H.; Suzuki, T.; Ando, M.; Hagiwara, H. Chem. Lett. 1999, 1245.
5. Schilling, B.; Kaiser, V.; Kaufmann, D. E. Chem. Ber. 1997, 130, 923.
6. Krishnamurti, R.; Kuivila, H. G.; Shaik, N. S.; Zubieta, J. Organometallics 1991, 10, 423.
7. Ishihara, K.; Inanaga, K.; Kondo, S.; Funahashi, M.; Yamamoto, H. Synlett 1998, 1053.
8. (a) Piers, W. E. Adv. Organomet. Chem. 2004, in press,
9. (b) Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527.
10. Blackwell, J. M.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 1295.
11. (a) Morrison, D. J.; Blackwell, J. M.; Piers, W. E. Pure Appl. Chem. 2004, 76, 615.
12. (b) Morrison, D. J.; Piers, W. E. Org. Lett. 2003, 5, 2857.
13. (a) Brown, K. J.; Berry, M. S.; Murdoch, J. R. J. Org. Chem. 1985, 50, 4345.
14. (b) Brown, K. J.; Berry, M. S.; Waterman, K. C.; Lingenfelter, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 4717.
15. 2O): δ = 28.8 (s).
16. (a) Frohn, H.-J.; Bailly, F.; Bardin, V. V. Z. Anorg. Allg. Chem. 2002, 628, 723.
17. (b) Frohn, H.-J.; Franke, H.; Fritzen, P.; Bardin, V. V. J. Organomet. Chem. 2000, 598, 127.
18. 21 = -4.8 (c 0.0080, acetone).
19. 3): δ = 23.6 (s).
20. 10: C, 64.74%; H, 2.47%. Found: C, 63.68%; H, 2.32%.
21. -3.
22. For recent examples and applications of aryl-perfluoroaryl interactions in crystal engineering see: (a) Gdaniec, M.; Jankowski, W.; Milewska, M. J.; Poloñski, T. Angew. Chem. Int. Ed. 2003, 42, 3903.
23. (b) Collings, J. C.; Roscoe, K. P.; Robins, E. G.; Batsanov, A. S.; Stimson, L. M.; Howard, J. A. K.; Clark, S. J.; Marder, T. B. New J. Chem. 2002, 26, 1740.
24. (c) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641.
25. R (S)-(-), 16.5 min, Daicel Chiralcel OD-H, hexane-2-PrOH = 19:1, 0.5 mL/ min]
26. R (R)-(+), 16.7 min, Daicel Chiralcel OD-H, hexane-2-PrOH = 9:1, 0.5 mL/min]
27. R (R)-(+), 27.5 min Daicel Chiralcel OD-H, hexane-2-PrOH = 9:1, 0.5 mL/min].
28. (d) Shimada, T.; Kina, A.; Hayashi, T. J. Org. Chem. 2003, 68, 6329.
29. -3.
30. Thalladi, V. R.; Weiss, H.-C.; Bläser, D.; Boese, R.; Nangia, A.; Desiraju, G. R. J. Am. Chem. Soc. 1998, 120, 8702.