The origin of atropisomerism in 2,2'-bis((1R,2R,4S)-2-hydroxy-1,3,3- trimethylbicyclo[2.2.1]hept-2-yl)-1,1'-biphenyl: Synthesis, structure and energetics

Tetrahedron

Volumn 56, Issue 6, 2000, Pages 881-884

  Goldfuss, Bernd ^a   Rominger, Frank ^a  

^a D 69120   (Germany)

Author keywords

Asymmetric induction; Biaryls; Bicyclic aliphatic compounds; Computer assisted methods

Indexed keywords

BIPHENYL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; HYDROGEN BOND; MOLECULAR STABILITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034602944     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01077-7     Document Type: Article

References (29)

1. Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. E21, p 5945.
2. (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. 1990, 102, 1006; Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
3. (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. 1990, 102, 1006; Angew. Chem., Int. Ed. Engl. 1990, 29, 977.
4. (b) Bringmann, G.; Breuning, M.; Walter, R.; Wuzik, A.; Peters, K.; Peters, E.-M. Eur. J. Org. Chem. 1999, 3047.
5. (c) Bringmann, G.; Breuning, M.; Tasler, S.; Endress, H.; Ewers, C. L. J.; Göbel, L.; Peters, K.; Peters, E.-M. Chem. Eur. J. 1999, 5, 3029.
6. (a) Braun, M. Angew. Chem. 1996, 108, 565; Angew. Chem., Int. Ed. Engl. 1996, 35, 519, and references therein.
7. (a) Braun, M. Angew. Chem. 1996, 108, 565; Angew. Chem., Int. Ed. Engl. 1996, 35, 519, and references therein.
8. (b) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473.
9. (c) Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 1383; Angew. Chem., Int. Ed. Engl. 1991, 30, 99.
10. (c) Schmidt, B.; Seebach, D. Angew. Chem. 1991, 103, 1383; Angew. Chem., Int. Ed. Engl. 1991, 30, 99.
11. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. 1997, 109, 1290; Angew. Chem., Int. Ed. Engl. 1997, 36, 1237.
12. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. 1997, 109, 1290; Angew. Chem., Int. Ed. Engl. 1997, 36, 1237.
13. (b) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
14. (a) Weber, E.; Wierig, A; Skobridis, K. J. Prakt. Chem./Chem.-Ztg. 1996, 338, 553.
15. (b) Weber, E.; Skobridis, K.; Wierig, A.; Stathi, S.; Nassimbeni, L. R.; Niven, M. L. Angew. Chem. 1993, 105, 616; Angew. Chem., Int. Ed. Engl. 1993, 32, 606.
16. (b) Weber, E.; Skobridis, K.; Wierig, A.; Stathi, S.; Nassimbeni, L. R.; Niven, M. L. Angew. Chem. 1993, 105, 616; Angew. Chem., Int. Ed. Engl. 1993, 32, 606.
17. (c) Toda, F.; Kai, A.; Toyotaka, R.; Yip, W.-H.; Mak, T. C. W. Chem. Lett. 1989, 1921.
18. Dimitrov V., Genov M., Simova S., Linden A. J. Organomet. Chem. 525:1996;213.
19. (a) Goldfuss, B.; Steigelmann, M.; Khan, S. I.; Houk, K. N. J. Org. Chem., 2000, 65, 77.
20. (b) Goldfuss, B.; Steigelmann, M.; Rominger, F. Eur. J. Org. Chem., in press.
21. (c) Goldfuss, B.; Steigelmann, M. J. Mol. Model., in press.
22. Goldfuss B., Khan S.I., Houk K.N. Organometallics. 18:1999;2927.
23. Crystallographic data have been deposited with the Cambridge Crystallographic Data Center.
24. In the X-ray crystal structure of 3 one and a half molecules appear in the asymmetric unit. While both molecules of 3 exhibit similar geometries, the hydrogen atom in the H-bond of the half molecule is disordered. The given geometric values hence refer to the complete molecule in the asymmetric unit.
25. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J., Jr.; A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.5; Gaussian: Pittsburgh, PA, 1998.
26. (b) Dapprich, S.; Komaromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. Theochem. 1999, 461-462, 1.
27. (a) Neugebauer, W.; Kos, A. J.; Schleyer, P. v. R. J. Organomet. Chem. 1982, 228, 107.
28. (b) Schubert, U.; Neugebauer, W.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1982, 1184.
29. (c) Neugebauer, W. Ph.D. Thesis, University Erlangen, 1983.