One-step stereoselective synthesis and NMR chiral shift properties of a novel hexacoordinated phosphorus cation

Organic Letters

Volumn 4, Issue 14, 2002, Pages 2309-2312

  Lacour, Jérôme ^a   Vial, Laurent ^a   Bernardinelli, Gerald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041307379     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026152b     Document Type: Article

References (45)

1. Von Zelewsky, A. Stereochemistry of Coordination Compounds; John Wiley & Sons: Chichester, UK, 1996. Gallagher, M. J.; Jenkins, I. D. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1968; Vol. 3, pp 76-79.
2. Von Zelewsky, A. Stereochemistry of Coordination Compounds; John Wiley & Sons: Chichester, UK, 1996. Gallagher, M. J.; Jenkins, I. D. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1968; Vol. 3, pp 76-79.
3. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
4. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
5. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
6. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
7. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
8. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
9. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
10. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
11. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
12. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
13. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
14. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
15. Hellwinkel, D. In Organic Phosphorus Compounds; Kosolapoff, G. M., Maier, L., Eds.; John Wiley & Sons: 1972; Vol. 3, pp 251-319. Luckenbach, R. In Methoden der Organischen Chemie. Band E2., 4th ed.; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1982; pp 897-907. Cherkasov, R. A.; Polezhaeva, N. A. Russ. Chem. Rev. 1987, 56, 163-181. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; John Wiley & Sons: New York, 1994; Vol. 3, pp 185-272. Holmes, R. R. Chem. Rev. 1996, 96, 927-950. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. Rev. 1996, 96, 1917-1951. Holmes, R. R. Acc. Chem. Res. 1998, 31, 535-542. Swamy, K. C. K.; Kumaraswamy, S.; Said, M. A.; Kishore, R. S. K.; Herbst-Irmer, R.; Pulm, M. Curr. Sci. 2000, 78, 473-478. Krill, J.; Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1997, 130, 1479-1483. Shevchenko, I. V.; Fischer, A.; Jones, P. G.; Schmutzler, R. Chem. Ber. 1992, 125, 1325-1332. Nakamoto, M.; Akiba, K.-Y. J. Am. Chem. Soc. 1999, 121, 6958-6959. Comotti, A.; Gallazzi, M. C.; Simonutti, R.; Sozzani, P. Chem. Mater. 1998, 10, 3589-3596. Skowronska, A.; Kowara, J.; Kaminski, R.; Bujacz, G.; Wieczorek, M. W. J. Org. Chem. 2000, 65, 304-315.
16. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
17. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
18. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
19. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
20. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
21. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
22. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1964, 86, 5132-5137. Muetterties, E. L.; Wright, C. M. J. Am. Chem. Soc. 1965, 87, 21-24. Schmidpeter, A.; Criegern, T. v.; Blanck, K. Z. Naturforsch., B: Chem. Sci. 1976, 31, 1058-1063. Schmidpeter, A.; Von Criegern, T.; Sheldrick, W. S.; Schomburg, D. Tetrahedron Lett. 1978, 2857-2860. Sheldrick, W. S.; Schmidpeter, A.; Von Criegern, T. Z. Naturforsch., B: Chem. Sci. 1978, 33, 583-587. Deng, R. M. K.; Dillon, K. B. J. Chem. Soc., Dalton Trans. 1984, 1917-1920. Potrzebowski, M. J.; Kowara, J.; Ciesielski, W.; Skowronska, A. J. Chem. Soc., Perkin Trans. 2 1995, 1149-1153.
23. Tris(tropyliumdiolato)silicate(iv) was however resolved; see: Inoue, T.; Sato, K. Bull. Chem. Soc. Jpn. 1973, 46, 2417-2420. Inoue, T. Inorg. Chem. 1983, 22, 2435-2439.
24. Tris(tropyliumdiolato)silicate(iv) was however resolved; see: Inoue, T.; Sato, K. Bull. Chem. Soc. Jpn. 1973, 46, 2417-2420. Inoue, T. Inorg. Chem. 1983, 22, 2435-2439.
25. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609. Lacour, J.; Ginglinger, C.; Favarger, F. Tetrahedron Lett. 1998, 4825-4828.
26. Lacour, J.; Ginglinger, C.; Grivet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 608-609. Lacour, J.; Ginglinger, C.; Favarger, F. Tetrahedron Lett. 1998, 4825-4828.
27. For large-scale preparation of tropolone, see: Minns, R. A. Org. Synth. 1977, 57, 117-121.
28. Dias, H. V. R.; Wang, Z.; Jin, W. Coord. Chem. Rev. 1998, 776, 67-86. Wong, C. Y.; Woolins, J. D. Coord. Chem. Rev. 1994, 130, 175-241. Evans, D. F.; Parr, J.; Wong, C. Y. Polyhedron 1992, 11, 567-572.
29. Dias, H. V. R.; Wang, Z.; Jin, W. Coord. Chem. Rev. 1998, 776, 67-86. Wong, C. Y.; Woolins, J. D. Coord. Chem. Rev. 1994, 130, 175-241. Evans, D. F.; Parr, J.; Wong, C. Y. Polyhedron 1992, 11, 567-572.
30. Dias, H. V. R.; Wang, Z.; Jin, W. Coord. Chem. Rev. 1998, 776, 67-86. Wong, C. Y.; Woolins, J. D. Coord. Chem. Rev. 1994, 130, 175-241. Evans, D. F.; Parr, J.; Wong, C. Y. Polyhedron 1992, 11, 567-572.
31. a1 = 10.87. See: Beauchamp, A.; Benoit, R. L. Can. J. Chem. 1966, 44, 1607-1614. Rosenblatt, D. H.; Epstein, J.; Levitch, M. J. Am. Chem. Soc. 1953, 75, 3277-3278.
32. a1 = 10.87. See: Beauchamp, A.; Benoit, R. L. Can. J. Chem. 1966, 44, 1607-1614. Rosenblatt, D. H.; Epstein, J.; Levitch, M. J. Am. Chem. Soc. 1953, 75, 3277-3278.
33. Lacour, J.; Londez, A.; Goujon-Ginglinger, C.; Buss, V.; Bernardinelli, G. Org. Lett. 2000, 2, 4185-4188.
34. Δ or Λ corresponds to the configuration of the P-centre, and δ or λ to the conformational isomerism of the binol ligand.
35. Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 303-322.
36. For the use of binol to control the configuration of metal complexes, see: Brunkan, N. M.; White, P. S.; Gagne, M. R. Angew. Chem., Int. Ed. 1998, 37, 1579-1582.
37. Lacour, J.; Barchéchath, S.; Jodry, J. J.; Ginglinger, C. Tetrahedron Lett. 1998, 39, 567-570.
38. Using racemic 5 as counterion, four bands could in principle be observed on TLC, corresponding to the four possible diastereomeric ion pairs [3M][Δ-5], [3M][Λ-5], [3m][Δ-5], and [3m][Λ-5]. However, it was not the case.
39. In the following experiments care was taken to use samples made all from (R)-binol, although this precaution is not necessary for the NMR experiments.
40. All recrystallization attempts with other solvents led to poorer quality crystals. The molecular packing shows "channels" in which are located the solvents molecules showing large disorders. Crystallographic data are available as Supporting Information.
41. Flack, H. D.; Bernardinelli, G. Acta Crystallogr. Sect. A 1999, 55, 908-915; J. Appl. Crystallogr. 2000, 33, 1143-1148.
42. Flack, H. D.; Bernardinelli, G. Acta Crystallogr. Sect. A 1999, 55, 908-915; J. Appl. Crystallogr. 2000, 33, 1143-1148.
43. 6, the signal of racemic TRISPHAT anion is not split by the chiral cation, as the polarity of the solvent medium most probably generates separated ion pairs.
44. Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc, Perkin Trans. 1 2000, 4403-4408. Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165-4168.
45. Green, S.; Nelson, A.; Warriner, S.; Whittaker, B. J. Chem. Soc, Perkin Trans. 1 2000, 4403-4408. Llewellyn, D. B.; Adamson, D.; Arndtsen, B. A. Org. Lett. 2000, 2, 4165-4168.