A new synthetic route to P-chiral phosphine-boranes of high enantiopurity via stereocontrolled Pd(0)-Cu(I) cocatalyzed aromatic phosphorylation

Journal of Organic Chemistry

Volumn 65, Issue 15, 2000, Pages 4776-4778

  Al Masum, Mohammad ^a   Kumaraswamy, G ^a   Livinghouse, Tom ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; COPPER; LEAD; PHOSPHINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; PHOSPHORYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034725879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0003605     Document Type: Article

References (30)

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5. (a) For a publication concerning the use of asymmetric deprotonation for the synthesis of P-chiral diphosphines, see: Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
6. (b) For the synthesis of P-chiral phosphine-boranes via dynamic resolution, see: Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
7. (c) For the use of crystallization-induced asymmetric transformation in this context, see: Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
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10. For an initial report concerning the use of the Cu(I)-Pd(0) cocatalyst system for the arylation of racemic methylphenylphosphineborane, see: Al-Masum, M.; Livinghouse, T. Tetrahedron Lett. 1999, 40, 7731.
11. Oshiki, T.; Imamoto, T. J. Am. Chem. Soc. 1992, 114, 3975.
12. For examples involving the Pd(0) catalyzed cross-coupling of enantioenriched isopropyl arylmethyl phosphinates see: (a) Zhang, J.; Xu, Y. J. Chem. Soc. Chem. Commun. 1988, 1606. (b) Zhang, J.; Xu, Y.; Huang, G.; Guo, H. Tetrahedron Lett. 1988, 29, 1955. (c) Xu, Y.; Wei, H.; Zhang, J.; Huang, G. Tetrahedron Lett. 1989, 30, 949.
13. For examples involving the Pd(0) catalyzed cross-coupling of enantioenriched isopropyl arylmethyl phosphinates see: (a) Zhang, J.; Xu, Y. J. Chem. Soc. Chem. Commun. 1988, 1606. (b) Zhang, J.; Xu, Y.; Huang, G.; Guo, H. Tetrahedron Lett. 1988, 29, 1955. (c) Xu, Y.; Wei, H.; Zhang, J.; Huang, G. Tetrahedron Lett. 1989, 30, 949.
14. For examples involving the Pd(0) catalyzed cross-coupling of enantioenriched isopropyl arylmethyl phosphinates see: (a) Zhang, J.; Xu, Y. J. Chem. Soc. Chem. Commun. 1988, 1606. (b) Zhang, J.; Xu, Y.; Huang, G.; Guo, H. Tetrahedron Lett. 1988, 29, 1955. (c) Xu, Y.; Wei, H.; Zhang, J.; Huang, G. Tetrahedron Lett. 1989, 30, 949.
15. 9
16. 18
17. Oshiki, T.; Hikosaka, T.; Imamoto, T. Tetrahedron Lett. 1991, 32, 3371.
18. 11 results in complete racemization: Kumaraswamy, G.; Livinghouse, T., unpublished observations.
19. Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
20. Oshiki, T.; Imamoto, T. Bull. Chem. Soc. Jpn. 1990, 63, 3719.
21. The presence of sub-stoichiometric quantities of CuI has been shown to increase the efficiency of certain Stille-type cross coupling reactions as well as Castro-Stevens alkynylations: (a) Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58, 408. (b) Myers, A. G.; Alauddin, M. M.; Fuhry, M. A. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997. (c) Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600. (d) Additional related work has been reported by Piers: Piers, E.; Romaro, M. A. J. Am. Chem. Soc. 1996, 118, 1215.
22. The presence of sub-stoichiometric quantities of CuI has been shown to increase the efficiency of certain Stille-type cross coupling reactions as well as Castro-Stevens alkynylations: (a) Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58, 408. (b) Myers, A. G.; Alauddin, M. M.; Fuhry, M. A. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997. (c) Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600. (d) Additional related work has been reported by Piers: Piers, E.; Romaro, M. A. J. Am. Chem. Soc. 1996, 118, 1215.
23. The presence of sub-stoichiometric quantities of CuI has been shown to increase the efficiency of certain Stille-type cross coupling reactions as well as Castro-Stevens alkynylations: (a) Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58, 408. (b) Myers, A. G.; Alauddin, M. M.; Fuhry, M. A. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997. (c) Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600. (d) Additional related work has been reported by Piers: Piers, E.; Romaro, M. A. J. Am. Chem. Soc. 1996, 118, 1215.
24. The presence of sub-stoichiometric quantities of CuI has been shown to increase the efficiency of certain Stille-type cross coupling reactions as well as Castro-Stevens alkynylations: (a) Liebeskind, L. S.; Riesinger, S. W. J. Org. Chem. 1993, 58, 408. (b) Myers, A. G.; Alauddin, M. M.; Fuhry, M. A. M.; Dragovich, P. S.; Finney, N. S.; Harrington, P. M. Tetrahedron Lett. 1989, 30, 6997. (c) Han, X.; Stoltz, B. M.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 7600. (d) Additional related work has been reported by Piers: Piers, E.; Romaro, M. A. J. Am. Chem. Soc. 1996, 118, 1215.
25. Representative cross-couplings that were conducted at higher temperatures (e.g., 25°C) resulted in lower product ee's.
26. 3N-mediated racemization of 1 was shown to be a comparatively slow process at 0°C.
27. 2P (3 equiv) in THF: Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1994, 59, 7195.
28. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
29. Enantiomeric purity was established by HPLC using a Chiralpak AD HPLC column.
30. 18 to that synthesized via Pd(0)-Cu-(I) cocatalyzed cross-coupling. It is also of significance that the sample of 3a prepared in this manner was obtained in lower enantiomeric purity and yield when compared to the present cross-coupling procedure.