New Copper and Rhodium Cyclopropanation Catalysts Supported by Chiral Bis(pyrazolyl)pyridines. A Metal-Dependent Enantioselectivity Switch

Organometallics

Volumn 14, Issue 5, 1995, Pages 2148-2150

  Christenson, David L ^a   Tokar, Christopher J ^a   Tolman, William B ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001095826     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00005a008     Document Type: Article

References (14)

1. Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 66, 497-526.
2. Pfaltz, A. Acc. Chem. Res. 1993, 26, 339–345. (b) Pflatz, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Springer-Verlag; Berlin, 1989; Vol. 5, pp 198-248.
3. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726–728. (b) Lowenthal, R. E.; Masamune, S. Tetrahedron Lett. 1991, 32, 7373—7376.
4. For recent reviews on catalytic asymmetric cyclopropanations, see: Doyle, M. P. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 63–99.
5. Itoh, K.; Itoh, Y.; Matsumoto, H.; Nishiyama, H.; Park, S.-B. J. Am. Chem. Soc. 1994, 116, 2223–2224.
6. LeCloux, D. D.; Tokar, C. J.; Osawa, M.; Houser, R. P.; Keyes, M. C.; Tolman, W. B. Organometallics 1994, 13, 2855–2866. (b) LeCloux, D. D.; Keyes, M. C.; Osawa, M.; Reynolds, V.; Tolman, W. B. Inorg. Chem. 1994, 33, 6361–6368.
7. Jameson, D. L.; Goldsby, K. A. J. Org. Chem. 1990, 50, 4992–4994.
8. LeCloux, D. D.; Tolman, W. B. J. Am. Chem. Soc. 1993, 115, 1153–1154.
9. Structurally analogous ruthenium complexes of achiral bis-(pyrazolyl)pyridines have been reported: Bessel, C.; See, R. F.; Jameson, D. L.; Churchill, M. R.; Takeuchi, K. J. J. Chem. Soc., Dalton Trans. 1993, 1563–1576.
10. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500–508. (b) Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K. Organometallics 1989, 8, 846–848.
11. Other examples of reversal of enantioselectivity in reactions performed with identical chiral auxiliaries: (a) Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc., Perkin Trans. 1 1989, 1571–1575. (b) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083–4084.
12. Fritschi, H.; Leutenegger, U.; Pflatz, A. Helv. Chim. Acta 1988, 71, 1553–1565.
13. Similar arguments may explain recent results obtained with catalysts complexed to chiral bi- and terpyridine ligands: Chelucci, G.; Cabras, M. A.; Saba, A. J. Mol. Catal. 1995, 95, L7-L10.
14. Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797–1815 and references cited therein.