Synthesis and characterization of novel ligands designed for secondary interactions

Organometallics

Volumn 15, Issue 2, 1996, Pages 483-485

  MacFarland, Darren K ^a   Landis, Clark R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000483291     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950819z     Document Type: Article

References (26)

1. (a) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
2. (b) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
3. (c) Burk, M. J. Organometallics 1990, 9, 2653.
4. (d) For recent reviews see: Noyori, R. Science 1990, 1194. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
5. (d) For recent reviews see: Noyori, R. Science 1990, 1194. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
6. For a review, see: Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
7. McLain, S. J. J. Am. Chem. Soc. 1983, 705, 6355.
8. Klang, J. A.; Collum, D. B. Organometallics 1988, 7, 1532.
9. (a) See Cation Binding by Macrocycles; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; and references therein.
10. (b) Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry: Cambridge, U.K., 1991.
11. (c) Izatt, R. M.; Bradshaw, J. S.; Neilsen, S. A.; Lamb, J. D.; Christensen, J. J.; Sen, D. Chem. Rev. 1985, 85, 271.
12. Wink, D. J.; Kwok, T. J.; Yee, A. Inorg. Chem. 1990, 29, 5006.
13. Kwok, T. J.; Wink, D. J. Organometallics 1993, 12, 1954.
14. Lukyanenko, N. G.; Reder, A. S.; Lyantseva, L. N. Synthesis 1986, 932.
15. The synthesis of the diamide (5) is based on a procedure in: Schmidt, M.; Amstutz, R.; Crass, G.; Seebach, D. Chem. Ber. 1980, 113, 1691.
16. Reduction of the diamide (5) is based on: Munoz, S.; Mallen, J.; Naxano, A.; Chen, Z.; Gay, I.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1993, 115, 1705.
17. 3): δ 68.9-70.4 (4 peaks) (OCCO), 68.7 (CH), 59.0 (NCC(OH)), 55.1 (NCCO).
18. 31P NMR: δ 171 (s).
19. + = m/e 585.
20. 2Pt: C, 41.94; H, 6.84; N, 3.62. Found: C, 41.64; H, 6.60; N, 3.12. 9a is a highly viscous oil with variable amounts of THF and ether as persistent contaminants.
21. Pt-P = 3100 Hz).
22. 195Pt is 33.8% abundant, I = 1/2, and yields a characteristic satellite "triplet" pattern.
23. 2 were used.
24. 1H NMR. Average rate: 10 ± 2 turnovers/h for all amides, n / i ratios are as follows: 1-butenamide, 0.9; 1-pentenamide, 3.3.
25. Buisman, G. J. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Asymmetry 1993, 4, 1625.
26. Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066.