Collect. Czech. Chem. Commun. 2003, 68, 1206-1232
https://doi.org/10.1135/cccc20031206

Synthesis and Catalytic Activity of Spaced Ferrocene Oxazolines

Petr Štěpničkaa,*, Tomáš Bašea, Ivana Císařováa, Jiří Kubištab, Štěpán Vyskočilc and Martin Štíchac

a Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
b J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 182 23 Prague 8, Czech Republic
c Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic

References

1a. Richards C. J., Locke A. J.: Tetrahedron: Asymmetry 1998, 9, 2377 (a comprehensive review). <https://doi.org/10.1016/S0957-4166(98)00251-1>
1b. For recent examples, see: You S.-L., Zhou Y.-G., Hou X.-L., Dai L.-X.: Chem. Commun. 1998, 2765. <https://doi.org/10.1039/a808267g>
1c. Park J., Quan Z., Lee S., Ahn K. H., Cho C.-W.: J. Organomet. Chem. 1999, 584, 140. <https://doi.org/10.1016/S0022-328X(99)00125-4>
1d. Malone Y. M., Guiry P. J.: J. Organomet. Chem. 2000, 603, 110. <https://doi.org/10.1016/S0022-328X(00)00183-2>
1e. Deng W.-P., You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W., Sun J.: J. Am. Chem. Soc. 2001, 123, 6508. <https://doi.org/10.1021/ja002657q>
1f. Takei I., Nishibayashi Y., Ishii I., Mizobe Y., Uemura S., Hidai M.: Chem. Commun. 2001, 2360. <https://doi.org/10.1039/b106435p>
1g. Miyake Y., Iwata T., Chung K.-G., Nishibayashi Y., Uemura S.: Chem. Commun. 2001, 2584. <https://doi.org/10.1039/b107904b>
1h. You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W.: J. Org. Chem. 2002, 67, 4684. <https://doi.org/10.1021/jo016330z>
1i. (1′-Phosphinoferrocenyl)oxazolines: Zhang W., Yoneda Y., Kida T., Nakatsuji Y., Ikeda I.: Tetrahedron: Asymmetry 1998, 9, 3371. <https://doi.org/10.1016/S0957-4166(98)00334-6>
1j. Drahoňovský D., Císařová I., Štěpnička P., Dvořáková H., Maloň P., Dvořák D.: Collect. Czech. Chem. Commun. 2001, 66, 588. <https://doi.org/10.1135/cccc20010588>
1k. See also: Chesney A., Bryce M. R., Chubb R. W. J., Batsanov A. S., Howard J. A. K.: Synthesis 1998, 413. <https://doi.org/10.1055/s-1998-2051>
2a. Patti A., Lotz M., Knochel P.: Tetrahedron: Asymmetry 2001, 12, 3375. <https://doi.org/10.1016/S0957-4166(02)00036-8>
2b. Moreno R. M., Bueno A., Moyano A.: J. Organomet. Chem. 2002, 660, 62. <https://doi.org/10.1016/S0022-328X(02)01737-0>
3. Sutcliffe O. B., Chesney A., Bryce M. R.: J. Organomet. Chem. 2001, 637–639, 134. <https://doi.org/10.1016/S0022-328X(01)00884-1>
4a. Zhang W., Shimanuki T., Kida T., Nakatsuji Y., Ikeda I.: Tetrahedron Lett. 1996, 37, 7995. <https://doi.org/10.1016/0040-4039(96)01791-1>
4b. Zhang W., Shimanuki T., Kida T., Nakatsuji Y., Ikeda I.: J. Org. Chem. 1999, 64, 6247. <https://doi.org/10.1021/jo9902998>
4c. Salter R., Pickett T. W., Richards C. J.: Tetrahedron: Asymmetry 1998, 9, 4239. <https://doi.org/10.1016/S0957-4166(98)00443-1>
4d. Locke A. J., Pickett T. E., Richards C. J.: Synlett 2001, 141. <https://doi.org/10.1055/s-2001-9718>
4e. Štěpnička P.: New J. Chem. 2002, 26, 567. <https://doi.org/10.1039/b109495p>
5a. Meyers A. I., Mihelich E. D.: Angew. Chem. 1976, 88, 321. <https://doi.org/10.1002/ange.19760881004>
5b. Grene T. W., Wuts P. G. M.: Protecting Groups in Organic Chemistry, 3rd ed., p. 434. Wiley, New York 1999.
6a. Houlton A., Jasim N., Roberts R. M. G., Silver J., Cunningham S., McArdle P., Higgins P.: J. Chem. Soc., Dalton Trans. 1992, 2235. <https://doi.org/10.1039/dt9920002235>
6b. Silver J., Miller J. R., Houlton A., Ahmet M. T.: J. Chem. Soc., Dalton Trans. 1994, 3355. <https://doi.org/10.1039/dt9940003355>
6c. Bosque R., López C., Sales J., Solans X., Font-Bardía M.: J. Chem. Soc., Dalton Trans. 1994, 735. <https://doi.org/10.1039/dt9940000735>
6d. Pal S. K., Alagesan K., Samuelson A. G., Pebler J.: J. Organomet. Chem. 1999, 575, 108. <https://doi.org/10.1016/S0022-328X(98)00983-8>
6e. Pal S. K., Krishnan A., Das P., Samuelson A. G.: J. Organomet. Chem. 2000, 604, 248. <https://doi.org/10.1016/S0022-328X(00)00278-3>
6f. also: Hecht E.: Z. Anorg. Allg. Chem. 2001, 627, 2351. <https://doi.org/10.1002/1521-3749(200110)627:10<2351::AID-ZAAC2351>3.0.CO;2-R>
7a. Meyers A. I., Temple D. L., Nolen R. L., Mihelich E. D.: J. Org. Chem. 1974, 39, 2778. <https://doi.org/10.1021/jo00932a022>
7b. Pridgen L. N., Miller G.: J. Heterocycl. Chem. 1983, 20, 1223. <https://doi.org/10.1002/jhet.5570200516>
8. Rossano L. T., Plata D. J., Kallmerten J.: J. Org. Chem. 1988, 53, 5189. <https://doi.org/10.1021/jo00256a065>
9. Oguni N., Omi T.: Tetrahedron Lett. 1984, 25, 2823. <https://doi.org/10.1016/S0040-4039(01)81300-9>
10. Soai K., Niwa S.: Chem. Rev. (Washington, D. C.) 1992, 92, 833. <https://doi.org/10.1021/cr00013a004>
11a. Butsugan Y., Araki S., Watanabe M. in: Ferrocenes (A. Togni and T. Hayashi, Eds), Chap. 3, p. 173. VCH, Weinheim 1995.
11b. Bolm C., Muñiz-Fernández K., Seger A., Raabe G., Günther K.: J. Org. Chem. 1998, 63, 7860. <https://doi.org/10.1021/jo981098r>
11c. Bolm C., Hermanns N., Hildebrand J. O., Muñiz K.: Angew. Chem., Int. Ed. 2000, 39, 3465. <https://doi.org/10.1002/1521-3773(20001002)39:19<3465::AID-ANIE3465>3.0.CO;2-4>
11d. Bolm C., Hermanns N., Kesselgruber M., Hildebrand J. P.: J. Organomet. Chem. 2001, 624, 157. <https://doi.org/10.1016/S0022-328X(00)00906-2>
12. Baše T., Císařová I., Štěpnička P.: Inorg. Chem. Commun. 2002, 5, 46. <https://doi.org/10.1016/S1387-7003(01)00346-X>
13. Structural data have been retrieved from the Cambridge structural database; refcode: KAPHOY: (Fc)C–CH2 1.507, FcCH2–NH 1.469, (4-MeC6H4)C–CH2 1.503, and (4-MeC6H4)CH2–N 1.448 Å; N–C–N 113.0°. Original reference: Hess A., Brosch O., Weyhermueller T., Metzler-Nolte N.: J. Organomet. Chem. 1999, 589, 75. <https://doi.org/10.1016/S0022-328X(99)00304-6>
14a. Nishibayashi Y., Segawa K., Arikawa Y., Ohe K., Hidai M., Uemura S.: J. Organomet. Chem. 1997, 545–546, 381. <https://doi.org/10.1016/S0022-328X(97)00368-9>
14b. Nishibayashi Y., Uemura S.: Synlett 1995, 1088.
14c. Park J., Lee S., Han K., Cho C.-W.: Tetrahedron Lett. 1996, 37, 6137. See also ref.11c. <https://doi.org/10.1016/0040-4039(96)01331-7>
15. Breit B.: J. Mol. Catal. A: Chem. 1999, 143, 143. <https://doi.org/10.1016/S1381-1169(98)00377-X>
16. Breton P., André-Barrès C., Langlois Y.: Synth. Commun. 1992, 22, 2543. <https://doi.org/10.1080/00397919208021650>
17. Westley J. W., Halpern B.: J. Org. Chem. 1968, 33, 3978. <https://doi.org/10.1021/jo01274a077>
18. Lopéz C., Bosque R., Solans X., Font-Bardía M., Tramuns D., Fern G., Silver G.: J. Chem. Soc., Dalton Trans. 1994, 3039. <https://doi.org/10.1039/dt9940003039>
19a. Otwinowski Z., Minor W.: HKL Denzo and Scalepack Program Package by Enraf–Nonius.
19b. For a reference, see: Otwinowski Z., Minor W.: Methods Enzymol. 1997, 276, 307. <https://doi.org/10.1016/S0076-6879(97)76066-X>
20. Altomare A., Burla M. C., Camalli M., Cascarano G., Giacovazzo C., Guagliardi A., Polidori G.: J. Appl. Crystallogr. 1994, 27, 435.
21. Sheldrick G. M.: SHELXL97. Program for Crystal Structure Refinement from Diffraction Data. University of Göttingen, Göttingen 1997.