Collect. Czech. Chem. Commun. 2000, 65, 539-548
https://doi.org/10.1135/cccc20000539

Synthesis of C2-Symmetrical [1,1'-Binaphthalene]-2,2'-diamines with Additional Chelating Groups Attached to the Nitrogen Atoms as Potential Ligands for Asymmetric Catalysis

Štěpán Vyskočila,*, Luděk Mecaa, Jiří Kubištab, Petr Maloňc and Pavel Kočovskýd,*

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, 182 23 Prague 8, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
d Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K.

References

1a. Noyori R., Tomino I., Tanimoto Y.: J. Am. Chem. Soc. 1979, 101, 3129. <https://doi.org/10.1021/ja00505a056>
1b. Noyori R.: Pure Appl. Chem. 1981, 53, 2315. <https://doi.org/10.1351/pac198153122315>
1c. Noyori R., Tomino I., Tanimoto Y., Nishizawa M.: J. Am. Chem. Soc. 1984, 106, 6709. <https://doi.org/10.1021/ja00334a041>
1d. For recent applications of BINOL and its congeners, see, e.g.: Pagenkopf B. L., Carreira E. M.: Chem. Eur. J. 1999, 5, 3437. <https://doi.org/10.1002/(SICI)1521-3765(19991203)5:12<3437::AID-CHEM3437>3.0.CO;2-E>
1e. Simonsen K. B., Svenstrup N., Robertson M., Jørgensen K. A.: Chem. Eur. J. 2000, 6, 123. <https://doi.org/10.1002/(SICI)1521-3765(20000103)6:1<123::AID-CHEM123>3.0.CO;2-L>
2a. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., Noyori R.: J. Am. Chem. Soc. 1980, 102, 7932. <https://doi.org/10.1021/ja00547a020>
2b. Takaya H., Akutagawa S., Noyori R.: Org. Synth. 1988, 67, 20.
2c. Noyori R., Takaya H.: Acc. Chem. Res. 1990, 23, 345. <https://doi.org/10.1021/ar00178a005>
3a. Smrčina M., Lorenc M., Hanuš V., Kočovský P.: Synlett 1991, 231. <https://doi.org/10.1055/s-1991-20688>
3b. Smrčina M., Lorenc M., Hanuš V., Sedmera P., Kočovský P.: J. Org. Chem. 1992, 57, 1917. <https://doi.org/10.1021/jo00032a055>
3c. Smrčina M., Poláková J., Vyskočil Š., Kočovský P.: J. Org. Chem. 1993, 58, 4534. <https://doi.org/10.1021/jo00069a010>
3d. Smrčina M., Vyskočil Š., Máca B., Polášek M., Claxton T. A., Abbott A. P., Kočovský P.: J. Org. Chem. 1994, 59, 2156. <https://doi.org/10.1021/jo00087a036>
3e. Smrčina M., Vyskočil Š., Hanuš V., Polášek M., Langer V., Chew B. G. M., Zax D. B., Verrier H., Harper K., Claxton T. A., Kočovský P.: J. Am. Chem. Soc. 1996, 118, 487. <https://doi.org/10.1021/ja951920y>
3f. Smrčina M., Vyskočil Š., Polívková J., Poláková J., Kočovský P.: Collect. Czech. Chem. Commun. 1996, 61, 1520. <https://doi.org/10.1135/cccc19961520>
3g. Smrčina M., Vyskočil Š., Polívková J., Poláková J., Sejbal J., Hanuš V., Polášek M., Verrier H., Kočovský P.: Tetrahedron: Asymmetry 1997, 8, 537. <https://doi.org/10.1016/S0957-4166(96)00539-3>
3h. Vyskočil Š., Smrčina M., Lorenc M., Hanuš V., Polášek M., Kočovský P.: Chem. Commun. 1998, 585. <https://doi.org/10.1039/a708213d>
3i. Vyskočil Š., Jaracz J., Smrčina M., Štícha M., Hanuš V., Polášek M., Kočovský P.: J. Org. Chem. 1998, 63, 7727. <https://doi.org/10.1021/jo9807565>
3j. Ding K., Xu Q., Wang Y., Liu J., Yu Z., Du B., Wu Y., Koshima H., Matsuura T.: Chem. Commun. 1997, 693. <https://doi.org/10.1039/a608256d>
3k. Mahmoud H., Han Y., Segal B. M., Cai L.: Tetrahedron: Asymmetry 1998, 9, 2035. <https://doi.org/10.1016/S0957-4166(98)00203-1>
3l. Singer R. A., Buchwald S. L.: Tetrahedron Lett. 1999, 40, 1095. <https://doi.org/10.1016/S0040-4039(98)02642-2>
3m. Ding K., Wang Y., Yun H., Liu J., Wu Y., Terada M., Okubo Y., Mikami K.: Chem. Eur. J. 1999, 5, 1734. <https://doi.org/10.1002/(SICI)1521-3765(19990604)5:6<1734::AID-CHEM1734>3.0.CO;2-G>
4a. Carreira E. M., Singer R. A., Wheeseong L.: J. Am. Chem. Soc. 1994, 116, 8837. <https://doi.org/10.1021/ja00098a065>
4b. Carreira E. M., Wheeseong L., Singer R. A.: J. Am. Chem. Soc. 1995, 117, 3649. <https://doi.org/10.1021/ja00117a049>
4c. Singer R. A., Carreira E. M.: J. Am. Chem. Soc. 1995, 117, 12360. <https://doi.org/10.1021/ja00154a049>
4d. Belokon Y. N., Kochetkov K. A., Churkina T. D., Ikonnikov N. S., Vyskočil Š., Kagan H. B.: Tetrahedron: Asymmetry 1999, 10, 1723. <https://doi.org/10.1016/S0957-4166(99)00185-8>
4e. For the corresponding methyl ether and imines derived from it, see: Knölker H.-J., Hermann H.: Angew. Chem., Int. Ed. Engl. 1996, 35, 341. <https://doi.org/10.1002/anie.199603411>
4f. Hungerhoff B., Metz P.: Tetrahedron 1999, 55, 14941. <https://doi.org/10.1016/S0040-4020(99)00978-3>
5a. Uozumi Y., Hayashi T.: J. Am. Chem. Soc. 1991, 113, 9887. <https://doi.org/10.1021/ja00026a044>
5b. For a review, see: Hayashi T.: Acta Chem. Scand. 1996, 50, 259. <https://doi.org/10.3891/acta.chem.scand.50-0259>
6a. Vyskočil Š., Smrčina M., Hanuš V., Polášek M., Kočovský P.: J. Org. Chem. 1998, 63, 7738. <https://doi.org/10.1021/jo980757x>
6b. Vyskočil Š., Smrčina M., Kočovský P.: Tetrahedron Lett. 1998, 39, 9289. <https://doi.org/10.1016/S0040-4039(98)02088-7>
6c. Kočovský P., Vyskočil Š., Císařová I., Sejbal J., Tišlerová I., Smrčina M., Lloyd-Jones G. C., Stephen S. C., Butts C. P., Murray M., Langer V.: J. Am. Chem. Soc. 1999, 121, 7714. <https://doi.org/10.1021/ja990309m>
6d. Aranyos A., Old D. W., Kiyomori A., Wolfe J. P., Sadighi J. P., Buchwald S. L.: J. Am. Chem. Soc. 1999, 121, 4369. <https://doi.org/10.1021/ja990324r>
6e. Hu X., Chen H., Zhang X.: Angew. Chem., Int. Ed. Engl. 1999, 38, 3518. <https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3518::AID-ANIE3518>3.0.CO;2-P>
6f. Fox J. M., Huang X., Chieffi A., Buchwald S. L.: J. Am. Chem. Soc. 2000, 122, 1360. <https://doi.org/10.1021/ja993912d>
7a. Rosini C., Franzini L., Raffaelli A., Salvadori P.: Synthesis 1992, 503. <https://doi.org/10.1055/s-1992-26147>
7b. Noyori R.: Asymmetric Catalysis in Organic Synthesis. Wiley & Sons, New York 1994.
7c. Putala M.: Enantiomer 1999, 4, 243.
8a. Nishida A., Yamanaka M., Nakagawa M.: Tetrahedron Lett. 1999, 40, 1555. <https://doi.org/10.1016/S0040-4039(98)02709-9>
8b. Denmark S. E., Su X., Nishigaichi Y., Coe D. M., Wong K.-T., Winter S. B. D., Choi J. Y.: J. Org. Chem. 1999, 64, 1958. <https://doi.org/10.1021/jo9820723>
8c. Jamieson J. Y., Schrock R. R., Davis W. M., Bonitatebus P. J., Zhu S. S., Hoveyda A.: Organometallics 2000, 19, 925. <https://doi.org/10.1021/om9908332>
8d. Reetz M. T., Haderlein G., Angermund K.: J. Am. Chem. Soc. 2000, 122, 996. <https://doi.org/10.1021/ja9930566>
8e. Radano C. P., Baker G. L., Smith III M. R.: J. Am. Chem. Soc. 2000, 122, 1552. <https://doi.org/10.1021/ja9930519>
8f. Reetz M. T., Bohres E., Goddard R.: Chem. Commun. 1999, 935.
8g. Zhang F.-Y., Pai C.-C., Chan A. S. C.: J. Am. Chem. Soc. 1998, 120, 5808. <https://doi.org/10.1021/ja974045k>
9. Miyano S., Nawa M., Mori A., Hashimoto H.: Bull. Chem. Soc. Jpn. 1984, 57, 2171. <https://doi.org/10.1246/bcsj.57.2171>
10. Vyskočil Š., Smrčina M., Kočovský P.: Collect. Czech. Chem. Commun. 1998, 63, 515. <https://doi.org/10.1135/cccc19980515>
11. Sakiyama H., Okawa H., Oguni N., Katsuki T., Irie R.: Bull. Chem. Soc. Jpn. 1992, 65, 606. <https://doi.org/10.1246/bcsj.65.606>
12. The reductive amination is sufficiently mild to prevent loss of enantiopurity of the intermediates and the final product (refs3i,10).
13a. Rosini C., Franzini L., Salvadori P., Spada G. P.: J. Org. Chem. 1992, 57, 6820. <https://doi.org/10.1021/jo00051a028>
13b. For a recent study of a series of binaphthyl derivatives, see: Di Bari L., Pescitelli G., Salvadori P.: J. Am. Chem. Soc. 1999, 121, 7998. <https://doi.org/10.1021/ja990326b>