Asymmetric activation of the Pd catalyst bearing the Tropos biphenylphosphine (BIPHEP) ligand with the chiral diaminobinaphthyl (DABN) activator

Organic Letters

Volumn 4, Issue 1, 2002, Pages 95-97

  Mikami, Koichi ^a   Aikawa, Kohsuke ^a   Yusa, Yukinori ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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ARTICLE;

EID: 0001910631     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0169675     Document Type: Article

References (22)

1. This work has been presented at the Annual Meeting of Chem. Soc. Jpn., March 31, 2001, No. 4H315.
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3. (b) Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; VCH: Weinheim, 1998.
4. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York. 1994.
5. (d) Brunner, H.; Zettlmeier, W.; Handbook of Enantio-selective Catalysis; VCH: Weinheim, 1993.
6. (e) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, 2000; Vols. I and II.
7. (f) Kagan, H. B. Comprehensive Organic Chemistry; Pergamon: Oxford, 1992; Vol. 8.
8. (g) Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff Publishers: Dordrecht, 1986.
9. Berrisford, D. J.; BoIm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
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11. (b) Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73. Review: Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532-3556.
12. (b) Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73. Review: Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532-3556.
13. (a) Ohkuma, T.; Doucet, H.; Pharm, T.; Mikami. K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
14. (b) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497.
15. (c) Mikami, K.; Korenaga, T.; Ohkuma, T.; Noyori, R. Angew. Chem., Int. Ed. 2000, 39, 3707-3710.
16. Hao, J.; Hatano, J.; Mikami, K. Org. Lett. 2000, 2, 4059-4062.
17. 2 = 0.1644. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-173070. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk). Selective bond lengths (Å) and bond and torsion angles (deg): Pd1-P1 2.283(17), Pd1-P2 2.288(15). Pd1-N1 2.16(5), Pd1-N2 2.17(5): P1-Pd1-P2 89.6(6), N1-Pd1-N2 84.2(19): C1-C2-C12-C11 63.88, C21-C22-C28-C27 67.06.
18. (a) Johannsen, M.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757.
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21. (d) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660-8667.
22. 2 (1 mL) was added ethyl glyoxylate (0.5 mmol) and 1,3-cyclohexadiene (0.75 mmol) at room temperature under an argon atmosphere. The reaction mixture was stirred at room temperature for 24 h, directly loaded onto a silica gel column, and eluted with hexane/ether (3:2) to give HDA product as a colorless oil.