Non-linear effects operate and dynamic ligand exchange occurs when chiral BINOL-boron Lewis acids are used for asymmetric catalysis

Tetrahedron Asymmetry

Volumn 14, Issue 14, 2003, Pages 1965-1968

  Cros, Jean Philippe ^a   Pérez Fuertes, Yolanda ^a   Thatcher, Michael J ^a   Arimori, Susumu ^a   Bull, Steven D ^a   James, Tony D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHOL; BORON DERIVATIVE; LEWIS ACID; NAPHTHOL DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; ION EXCHANGE; ISOMERISM; MOLECULAR PROBE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0038160033     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00352-5     Document Type: Article

References (32)

1. (a) James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 218, 159; (b) The increase in boron Lewis acidity for cyclic boronate esters over their corresponding acyclic analogues has been ascribed to the change in the O-B-O bond angle from 120° to around 108° for the cyclic system. For detailed discussion of this phenomenon, see: Ref. 1(a).
2. (a) James, T. D.; Shinkai, S. Top. Curr. Chem. 2002, 218, 159; (b) The increase in boron Lewis acidity for cyclic boronate esters over their corresponding acyclic analogues has been ascribed to the change in the O-B-O bond angle from 120° to around 108° for the cyclic system. For detailed discussion of this phenomenon, see: Ref. 1(a).
3. Hattori K., Yamamoto H. J. Org. Chem. 57:1992;3264.
4. Hattori K., Yamamoto H. Tetrahedron. 49:1993;1749.
5. Hattori K., Yamamoto H. Synlett. 1993;129.
6. Lock R., Waldmann H. Tetrahedron Lett. 37:1996;2753.
7. Lock R., Waldmann H. Chem. Eur. J. 3:1997;143.
8. Hattori K., Miyata M., Yamamoto H. J. Am. Chem. Soc. 115:1993;1151.
9. Hattori K., Yamamoto H. Synlett. 1993;239.
10. Hattori K., Yamamoto H. Bioorg. Med. Chem. Lett. 3:1993;2337.
11. Hattori K., Yamamoto H. Tetrahedron. 50:1994;2785.
12. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
13. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
14. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
15. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
16. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
17. For selected examples of other chiral boron reagents derived from enantiopure BINOL (and its derivatives) for asymmetric catalysis, see: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510; (b) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561; (c) Umemoto, T.; Adachi, K. J. Org. Chem. 1994, 59, 5692; (d) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049; (e) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026; (f) Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.
18. Ishihara K., Miyata M., Hattori K., Tada T., Yamamoto H. J. Am. Chem. Soc. 116:1994;10520.
19. For other examples where BLA complex (R,R)-8 (and structural analogues) have been employed as chiral Lewis acids for asymmetric catalysis, see: (a) Ishihara, K.; Kuroki, Y.; Yamamoto, H. Synlett 1995, 41; (b) Kawate, T.; Yamada, H.; Matsumizu, M.; Nishida, A.; Nakagawa, M. Synlett 1997, 761; (c) Yamada, H.; Kawate, T.; Matsumizu, M.; Nishida, A.; Yamaguchi, K.; Nakagawa, M. J. Org. Chem. 1998, 63, 6348.
20. For other examples where BLA complex (R,R)-8 (and structural analogues) have been employed as chiral Lewis acids for asymmetric catalysis, see: (a) Ishihara, K.; Kuroki, Y.; Yamamoto, H. Synlett 1995, 41; (b) Kawate, T.; Yamada, H.; Matsumizu, M.; Nishida, A.; Nakagawa, M. Synlett 1997, 761; (c) Yamada, H.; Kawate, T.; Matsumizu, M.; Nishida, A.; Yamaguchi, K.; Nakagawa, M. J. Org. Chem. 1998, 63, 6348.
21. For other examples where BLA complex (R,R)-8 (and structural analogues) have been employed as chiral Lewis acids for asymmetric catalysis, see: (a) Ishihara, K.; Kuroki, Y.; Yamamoto, H. Synlett 1995, 41; (b) Kawate, T.; Yamada, H.; Matsumizu, M.; Nishida, A.; Nakagawa, M. Synlett 1997, 761; (c) Yamada, H.; Kawate, T.; Matsumizu, M.; Nishida, A.; Yamaguchi, K.; Nakagawa, M. J. Org. Chem. 1998, 63, 6348.
22. Formation of (R)-6a-e may occur via an alternative tandem Mannich-conjugate addition pathway, however these reactions are described as formal aza-Diels-Alder reactions for clarity and consistency with the terminology used in Refs. 2a,b. For a fuller discussion on the mechanism of these reactions, see: (a) Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444; (b) Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309 and references cited therein.
23. Formation of (R)-6a-e may occur via an alternative tandem Mannich-conjugate addition pathway, however these reactions are described as formal aza-Diels-Alder reactions for clarity and consistency with the terminology used in Refs. 2a,b. For a fuller discussion on the mechanism of these reactions, see: (a) Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444; (b) Yuan, Y.; Li, X.; Ding, K. Org. Lett. 2002, 4, 3309 and references cited therein.
24. See Ref. 4 in Ref. 2a.
25. For recent reviews on non-linear effects in asymmetric catalysis, see: (a) Kagan, H. B. Synlett 2001, 888; (b) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
26. For recent reviews on non-linear effects in asymmetric catalysis, see: (a) Kagan, H. B. Synlett 2001, 888; (b) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
27. -1, which gave baseline resolution with elution times for (R)-6a of 33 min, and (S)-6a of 36 min.
28. For a previous example where addition of scalemic (R)-BINOL to borane resulted in kinetic resolution via selective formation of homochiral 3:2 BINOL-boron complex (R,R,R)-9 in enantiomerically enriched form, see: Ref. 5f.
29. For a review on ligand accelerated catalysis, see: Berrisford D.J., Bolm C., Sharpless K.B. Angew. Chem., Int. Ed. Engl. 34:1995;1059.
30. The theoretical value of 7.7% e.e. for (R)-6a is calculated from 10% of 77% e.e. obtained for (R)-6a using a chiral boron reagent (R)-3a derived from (R)-BINOL (100% e.e.).
31. For an overview on the concept of atom-efficiency in chemical reactions, see: Trost B.M. Angew. Chem., Int. Ed. Engl. 34:1995;259.
32. Use of 10 mol% of (R)-3a as catalyst for the aza-Diels-Alder reaction between 4a and 5 resulted in formation of (R)-6a in less than 5% yield.