Dynamic asymmetric catalysis by diphenylphosphinoferrocene (DPPF)-nickel complexes through control of axial chirality by chiral diamines

Organic Letters

Volumn 4, Issue 1, 2002, Pages 99-101

  Mikami, Koichi ^a   Aikawa, Kohsuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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EID: 0003106821     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016968x     Document Type: Article

References (25)

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3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. (d) Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis; VCH: Weiheim, 1993.
5. (e) Catalytic Asymmetric Synthesis; Ojima, L, Ed.; VCH: New York, 1993, 2000; Vois. I and II.
6. (f) Kagan, H. B. Comprehensive Organic Chemistry; Pergamon: Oxford, 1992; Vol. 8.
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8. Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995. Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis, Hassner, A., Ed.; JAI Press: London, Vol. 2, pp 189-235, 1997. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. Metallocene; Togni, A.; Halterman, R. L., Eds.: Wiley-VCH: Weinheim, 1998.
9. Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995. Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis, Hassner, A., Ed.; JAI Press: London, Vol. 2, pp 189-235, 1997. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. Metallocene; Togni, A.; Halterman, R. L., Eds.: Wiley-VCH: Weinheim, 1998.
10. Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995. Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis, Hassner, A., Ed.; JAI Press: London, Vol. 2, pp 189-235, 1997. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. Metallocene; Togni, A.; Halterman, R. L., Eds.: Wiley-VCH: Weinheim, 1998.
11. Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, 1995. Kagan, H. B.; Riant, O. In Advances in Asymmetric Synthesis, Hassner, A., Ed.; JAI Press: London, Vol. 2, pp 189-235, 1997. Richards, C. J.; Locke, A. J. Tetrahedron: Asymmetry 1998, 9, 2377. Metallocene; Togni, A.; Halterman, R. L., Eds.: Wiley-VCH: Weinheim, 1998.
12. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4421-4226 and references therein. For leading references, see: Deng, W.; You, S.; Hou, X.; Dai, L.; Yu, Y.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508-6519.
13. Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4421-4226 and references therein. For leading references, see: Deng, W.; You, S.; Hou, X.; Dai, L.; Yu, Y.; Xia, W.; Sun, J. J. Am. Chem. Soc. 2001, 123, 6508-6519.
14. 2: Casellato, U.; Ajo, D.; Valle, G.; Corain, B.; Longato, B.; Graziani, R. J. Crvstallogr. Spectrosc. Res. 1988, 18, S83-S90.
15. 2: Casellato, U.; Ajo, D.; Valle, G.; Corain, B.; Longato, B.; Graziani, R. J. Crvstallogr. Spectrosc. Res. 1988, 18, S83-S90.
16. 2: Casellato, U.; Ajo, D.; Valle, G.; Corain, B.; Longato, B.; Graziani, R. J. Crvstallogr. Spectrosc. Res. 1988, 18, S83-S90.
17. (a) Kanemasa, S.; Oderanotoshi, Y.; Sakaguchi, S.; Yamamoto, H.; Tanaka, J.; Wada, E.; Curran, D. P. J. Am. Chem. Soc. 1998, 120, 3074-3088.
18. (b) Iwasa, S.; Tsushima, S.; Shimada, T.; Nishiyama, H. Tetrahedron Lett. 2001, 42, 6715-6717.
19. We denote the dppf chirality in terms of descriptors of chirality sense of a helix: (P) plus, clockwise; (M) minus, counterclockwise.
20. 2, 300 MHz) δ 4.21 (br, 4H), 4.52 (br s, 2H), 4.58 (br s, 2H), 4.66 (br s, 2H), 4.85 (br s, 2H), 6.73 (d, J = 9.0 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H), 7.30 (t, J = 8.1 Hz, 2H), 7.39-7.44 (m, 4H), 7.54-7.67 (m, 8H), 7.76-7.81 (m, 4H), 7.85-7.94 (m, 6H), 8.05 (d, J = 8.1 Hz, 2H), 8.11 (d. J = 9.0 Hz, 2H).
21. max = 31.5°) were used for the solution of the structure. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. R = 0.0444, wR2 = 0.1218. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication N lo. CCDC-173071. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB21EZ, U.K. (Fax: (+44) 1223-336-033. E-mail deposit@ccdc.cam.ac.uk) Selective bond lengths [Å], bond angles [deg] and torsion angles [deg]: Pd1-P1 2.3036-(9), Pd1-P2 2.2904(9), Pd1-N1 2.169(3), Pd1-N2 2.152(3); P1-Pd1-P2 94.87(3), N1-Pd1-N2 83.53(11): C1-C10-C11-C20 65.92, P1-C33-C42-P2 34.86.
22. 2 complexes, see: Kelly. R. D.; Young, G. B. Polyhedron 1989, 8, 433-435. Ankianiec, B. C.; Young, G. B. Polyhedron 1991, 12, 1411-1421.
23. 2 complexes, see: Kelly. R. D.; Young, G. B. Polyhedron 1989, 8, 433-435. Ankianiec, B. C.; Young, G. B. Polyhedron 1991, 12, 1411-1421.
24. 2: Oi, S.; Kashiwagi, E.; Terada, E.; Ohuchi, K.; Inoue, Y. Tetrahedron Lett. 1996, 37, 6351-6354.
25. 2 (2 mL) was added (R)-DABN (0.022 mmol) at room temperature under argon atmosphere. After the mixture was stirred at room temperature for 1 h, ethyl glyoxylate (0.5 mmol) and alkene (0.4 mmol) were added and stirred for 24 h. The reaction mixture was directly loaded onto a silica gel column and eluted with hexane/AcOEt (3:1) to give the ene product as an colorless oil.