BINOL - Salen Metal Catalysts Incorporating a Bifunctional Design

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1641-1644

  DiMauro, Erin F ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS;

EID: 0035979038     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0158213     Document Type: Article

References (29)

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9. For reviews on bifunctional catalysis, see: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985-13011. Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
10. For reviews on bifunctional catalysis, see: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985-13011. Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
11. For reviews on bifunctional catalysis, see: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871. van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54, 12985-13011. Rowlands, G. J. Tetrahedron 2001, 57, 1865-1882.
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13. (b) Arai, T.; Hu, Q.; Zheng, X.; Pu, L.; Sasai, H. Org. Lett. 2000, 2, 4261-4263.
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15. (d) Sundararajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389-392.
16. Zn·Li: (e) Nina, S.; Soai, K. J. Chem. Soc., Perkin Trans. 1 1991, 2717-2720.
17. (a) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
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20. (d) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57, 805-814 and references therein.
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22. Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000 122, 2252-2260.
23. The BINOL portion of salen 13 is anticipated to create a chiral conformation in the achiral diamme portion. See: Balsells, J.; Walsh, P. J. J. Am. Chem. Soc. 2000, 122, 1802-1803.
24. In the second structure in the unit cell, the ancilliary naphthols adopt a nonparallel arrangement while most of the other features are the same as the first structure. Once again, one naphthoate oxygen is above the plane and one below the plane of the salen; however, only one of the naphthols forms an intramolecular hydrogen bond with the salen nucleus. The second naphthol participates in an intermolecular hydrogen bond with a naphthoate oxygen from the other complex in the unit cell. See Supporting Information for full details.
25. For recent reviews, see: (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: New York, 1999; Chapter 31.
26. (b) Leonard, J.; Ciez-Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 2051-2061.
27. 3CN, DMF), THF gave the best results.
28. 3).
29. Reaction time was 48 h at 20 and 0°C and 5 d at -20 and -40°C.