Fine-tuning monophosphine ligands for enhanced enantioselectivity. Influence of chiral hemilabile pendant groups

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1515-1517

  Zhang, Aibin ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DIOXANE DERIVATIVE; LIGAND; NICKEL COMPLEX; PHOSPHINE DERIVATIVE; PHOSPHORUS DERIVATIVE; STYRENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; MODEL;

CATALYSIS; LIGANDS; MOLECULAR CONFORMATION; NICKEL; PHOSPHINES; STEREOISOMERISM; STYRENES;

EID: 2442547591     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0495063     Document Type: Article

References (19)

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3. (a) For recent reviews dealing with this topic, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197. (e) For a compilation of more recent references, see, Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
4. (a) For recent reviews dealing with this topic, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354. Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197. (e) For a compilation of more recent references, see, Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
5. (a) For recent reviews dealing with this topic, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197. (e) For a compilation of more recent references, see, Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
6. (a) For recent reviews dealing with this topic, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197. (e) For a compilation of more recent references, see, Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
7. (a) For recent reviews dealing with this topic, see: (a) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315. (b) Hayashi, T. Acc. Chem. Res. 2000, 33, 354. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346. (d) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197. (e) For a compilation of more recent references, see, Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
8. (a) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459.
9. (b) RajanBabu, T. V.; Nomura, N.; Jin, J.; Nandi, M.; Park, H.; Sun, X. J. Org. Chem. 2003, 68, 8431.
10. RajanBabu, T. V. Chem. Rev. 2003, 103, 2845.
11. For use of hemilabile ligands in related reactions, see: Meking, S.; Keim, W. Organometallics 1996, 15, 2650 and references therein.
12. Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
13. For selected examples of monophosphines with chiral side chains, see: (a) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988,110, 8153. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889. Also see refs 2c and 3b. Many examples of the effects of chirality of one or other atom of a chelating ligand are known. For a recent example, see: Shintani, R.; Fu, G. C. Org. Lett. 2002, 4, 3699.
14. For selected examples of monophosphines with chiral side chains, see: (a) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988,110, 8153. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889. Also see refs 2c and 3b. Many examples of the effects of chirality of one or other atom of a chelating ligand are known. For a recent example, see: Shintani, R.; Fu, G. C. Org. Lett. 2002, 4, 3699.
15. For selected examples of monophosphines with chiral side chains, see: (a) Hayashi, T.; Hayashizaki, K.; Kiyoi, T.; Ito, Y. J. Am. Chem. Soc. 1988,110, 8153. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889. (c) Also see refs 2c and 3b. Many examples of the effects of chirality of one or other atom of a chelating ligand are known. For a recent example, see: Shintani, R.; Fu, G. C. Org. Lett. 2002, 4, 3699.
16. Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
17. Feringa's phosphoramidites, a class of BINAPO-derived ligands useful for asymmetric hydrovinylation, give only a low yield of the product (28% yield, 68% ee) in the hydrovinylation of 4-isobutylstyrene. Franció, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736.
18. This model assumes the involvement of diastereomeric (phosphorus/ olefin) cis and trans square planar transition states for the Ni-H addition to the prochiral faces of the olefin. While the cis-P/olefin complex appears to have a clear choice for the re-face addition, for the trans P/olefin complex there is no such preference. Our conjecture is that additional elements of chirality at the hemilabile position would favor one or other of these addition modes leading to increased selectivity.
19. See the Supporting Information for full experimental details, characterization, and analytical data including chromatographic traces of products.