Asymmetric Synthesis of Rigid C2-Symmetric Bis(ferrocenyl) Diol and Diamine Ligands

Organometallics

Volumn 18, Issue 24, 1999, Pages 5157-5162

  Larsen, Andrew O ^a   Taylor, Rebecca A ^a   White, Peter S ^a   Gagné, Michel R ^a  

^a The University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000550027     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9905512     Document Type: Article

References (34)

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11. For an alternative approach to a diastereomerically pure α-lithiated ferrocenecarboxaldehyde equivalent, see: (a) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (b) Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629-1635.
12. For an alternative approach to a diastereomerically pure α-lithiated ferrocenecarboxaldehyde equivalent, see: (a) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (b) Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629-1635.
13. Diagnostic for the selectivity of the coupling is the acetal hydrogen, which indicated that in the crude material the desired product was the major diastereoisomer (65%) along with 27% of unreacted starting material.
14. Patti, A.; Lambusta, D.; Piatelli, M.; Nicolosi, G. Tetrahedron: Asymmetry 1998, 9, 3073-3080.
15. Kündig, E. P.; Xu, L. H.; Romanens, P.; Bernardinelli, G. Synlett 1996, 270-272.
16. See footnote 2 and: (a) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775-12788.
17. (a) Santora, B. P.; Larsen, A. O.; Gagné, M. R. Organometallics 1998, 17, 3138-3140.
18. (b) Santora, B. P.; White, P. S.; Gagné, M. R. Organometallics 1999, 18, 2557-2560.
19. Larsen, A. O.; White, P. S.; Gagné, M. R. Inorg. Chem. 1999, 38, 4824-4828.
20. While the structure only allowed anisotropic thermal parameters to be modeled on the heavy atoms, the structure was sufficient to unambiguously assign connectivity, relative, and absolute stereochemistry (Table 1).
21. 2
22. See the Supporting Information for full tables of metrical parameters.
23. (a) Andrews, M. A.; Voss, E. J.; Gould, G. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 5730-5740.
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26. Pt-H couplings of 10-60 Hz; see for example: (a) Becker, J. J.; White, P. S.; Gagné, M. R. Inorg. Chem. 1999, 38, 798-801. (b) Appleton, T. G.; Hall, J. R. Inorg. Chem. 1971, 10, 1717-1725. (c) Erickson, L. E.; McDonald, J. W.; Howie, J. K.; Clow, R. P. J. Am. Chem. Soc. 1968, 90, 6371-6382.
27. Pt-H couplings of 10-60 Hz; see for example: (a) Becker, J. J.; White, P. S.; Gagné, M. R. Inorg. Chem. 1999, 38, 798-801. (b) Appleton, T. G.; Hall, J. R. Inorg. Chem. 1971, 10, 1717-1725. (c) Erickson, L. E.; McDonald, J. W.; Howie, J. K.; Clow, R. P. J. Am. Chem. Soc. 1968, 90, 6371-6382.
28. Pt-H couplings of 10-60 Hz; see for example: (a) Becker, J. J.; White, P. S.; Gagné, M. R. Inorg. Chem. 1999, 38, 798-801. (b) Appleton, T. G.; Hall, J. R. Inorg. Chem. 1971, 10, 1717-1725. (c) Erickson, L. E.; McDonald, J. W.; Howie, J. K.; Clow, R. P. J. Am. Chem. Soc. 1968, 90, 6371-6382.
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32. 2 was synthesized by refluxing Cu(II) carbonate basic with 4 equiv of pivalic acid in MeOH for 12 h, filtering, recrystallizing from MeOH, and drying under high vacuum. For several recent oxidative couplings of an alkyllithium using this reagent see: (a) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 111, 9075-9076. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001.
33. 2 was synthesized by refluxing Cu(II) carbonate basic with 4 equiv of pivalic acid in MeOH for 12 h, filtering, recrystallizing from MeOH, and drying under high vacuum. For several recent oxidative couplings of an alkyllithium using this reagent see: (a) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 111, 9075-9076. (b) Corey, E. J.; Chen, Z.; Tanoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000-11001.
34. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. Organometallics 1996, 15, 1518-1520.