Synthesis and Resolution of Quinazolinone Atropisomeric Phosphine Ligands

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2597-2600

  Dai, Xuedong ^a   Wong, Audrey ^a   Virgil, Scott C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001355777     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972105z     Document Type: Article

References (25)

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14. 1 space group with cell dimensions a = 10.4822(7) Å, b = 17.3192(12) Å, c = 18.5003(12) Å, and Z = 4. A total of 13 752 reflections were collected at -85°C using a Siemens SMART/CCD diffractometer. Least-squares refinement of the data using 4839 reflections converged upon the structure shown in Figure 1 with R = 0.0308 and a goodness of fit = 1.114.
15. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994.
16. Perrin, D. D. Dissociation Constants of Organic Bases in Aqueous Solution; International Union of Pure and Applied Chemistry: London, 1965; p 227.
17. Kashima, C.; Katoh, A. J. Chem. Soc., Perkin Trans. 1 1980, 1599.
18. 1 space group with cell dimensions a = 11.1602(5) Å, b = 10.8868(5) Å, c = 27.2325(12) Å, β = 95.132°, and Z = 2. A total of 8796 reflections were collected at 20 °C using a Siemens SMART/CCD diffractometer. Least-squares refinement of the data using 4690 reflections converged upon the structure shown in Figure 2 with R = 0.1176 and a goodness of fit = 1.044.
19. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
20. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
21. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
22. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
23. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
24. For examples of quasi-racemates, see: (a) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; Chapter 5. (b) Fredga, A. Tetrahedron 1960, 8, 126. (c) Auburn, M.; Ciriano, M.; Howard, J. A. K.; Murry, M.; Pugh, N. J.; Spencer, J. L.; Stone, F. G. A.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 659. (d) Schurig, V.; Pille, W.; Winter, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 327. (e) Alcock, N. W.; Hulmes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395. (f) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
25. 1H NMR analysis of the ratio of the palladium complex 6 and its diastereomer in the region of 3.5-7.0 ppm.