New chiral ligands for the asymmetric copper catalyzed conjugate addition of grignard reagents to enones

Tetrahedron

Volumn 53, Issue 48, 1997, Pages 16503-16510

  Stangeland, Eric L ^a   Sammakia, Tarek ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FERROCENE;

CATALYSIS; CHIRALITY; CONFERENCE PAPER; CONJUGATION; LIGAND BINDING; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030731638     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01031-4     Document Type: Conference Paper

References (38)

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13. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745; Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995.
14. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745; Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995.
15. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745; Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995.
16. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745; Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995.
17. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486; Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745; Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419; Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995.
18. (a) For a recent review, see: Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
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34. The best separation of the diastereomers was observed using a chiral stationary phase (β-cyclodextrin). The absolute configuration of the product was determined by comparison of the optical rotation of our product with that reported by Seebach See: Langer, W.; Seebach, D. Helv. Chim. Acta 1979, 62, 1710.
35. We examined two other solvents with this ligand, methyl-tert-butyl ether (MTBE) and iso-propyl ether and found both to be inferior to ethyl ether. In the case of MTBE, the enantioselectivity was slightly dimished (72% ee) whereas with iso-propyl ether the CuI-ligand complex did not dissolve, and we observed 13% conjugate addition and no enantioselectivity.
36. All yields refer isolated yields of homogenous products purified by flash chroatography.
37. Other workers have prepared this substrate and assigned the stereochemistry as we have. However, we consider this assignment as tentative since we could find no definitive stereochemical assignment of 3-n-butyl-cyclopentanone. Pfaltz has assigned the (+) isomer the (R)-configuration based on the observed Cotton effect.
38. Prepared according to the procedure reported by Storhoff, B. N.; Harper, D. P.; Saval, I. H.; Worstell, J. H. J. Organomet. Chem. 1981, 205, 161.