Regio- and stereoselective ring opening of 2,3-diaryl oxiranes by LiBr/Amberlyst 15: A new stereocontrolled access to 1,2-diaryl-2-bromo alcohols

Journal of Organic Chemistry

Volumn 70, Issue 5, 2005, Pages 1605-1611

  Solladié Cavallo, Arlette ^a   Lupattelli, Paolo ^b   Bonini, Carlo ^b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIFORNIUM; ELECTRON SCATTERING; LITHIUM COMPOUNDS; PROTONS;

ELECTRON-WITHDRAWING GROUPS; RING OPENING; STEREOSELECTIVITY;

AROMATIC COMPOUNDS;

2,3 DIARYLOXIRANE; CATION; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; LITHIUM; TRANS STILBENE OXIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL STRUCTURE; ELECTRON; MOLECULAR STABILITY; RING OPENING; STEREOCHEMISTRY; TEMPERATURE; THERMODYNAMICS;

BENZYL ALCOHOLS; BROMIDES; ETHYLENE OXIDE; LITHIUM COMPOUNDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 14544287742     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048045w     Document Type: Article

References (35)

1. (a) See: Halohydrines and derivatives. In Fiesers' Reagents for Organic Synthesis; Smith, J. G., Fieser, M., Eds.; New York, 1990.
2. (b) Bonini, C.; Righi, G. Synthesis 1994, 225.
3. (c) Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; pp 508-509.
4. (a) Xu, L.-W.; Li, L.; Xia, C.-G.; Zhao, P.-Q. Tetrahedron Lett. 2004, 45, 2435-2438.
5. (b) Paek, S. H.; Shim, S. C.; Cho, C. S.; Kim, T.-J. Synlett 2003, 849-851.
6. (c) Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827-8829.
7. (a) Soroka, M.; Goldeman, W.; Malysa, P.; Stochaj, M. Synthesis 2003, 2341-2344.
8. (b) Shargi, H.; Eskandari, M. M. Tetrahedron 2003, 53, 8509-8514.
9. (c) Shargi, H.; Paziraee, Z.; Niknam, K. Bull. Korean Chem. Soc. 2002, 23, 1611-1615.
10. (d) Diaz, D.; Martin, T.; Martin, V. S. J. Org. Chem. 2001, 66, 7231-7233.
11. (a) Guindon, Y.; Therien, M.; Girard, Y.; Yoakim, C. J. Org. Chem. 1987, 52, 1680-1686.
12. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246-6248.
13. (c) Bell, T. W.; Ciaccio, J. A.; Heller, E.; Talbot, A. Synlett 1991, 248-250.
14. (a) Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845-1848.
15. (b) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaio, L. J. Org. Chem. 2001, 66, 4463-4467.
16. (c) Sabitha, S.; Satheesh, R.; Rajkumar, M.; Reddy, Ch. S.; Yadav, J. S. Tetrahedron Lett. 2001, 42, 3955-3958.
17. (a) Konaklieva, M. I.; Dah, M. L.; Turos, E. Tetrahedron Lett. 1992, 33, 7093-7096.
18. (b) Sharghi, H.; Natimi, H. Bull. Chem. Soc. Jpn. 1999, 72, 1525-1531.
19. Yadav, J. S.; Reddy, B. V.; Reddy, Ch. S.; Rajasekhar, K. Chem. Lett. 2004, 33, 476-477.
20. See: Righi, G.; Pescatore, G.; Bonadies, F.; Bonini, C. Tetrahedron 2001, 57, 649-5656 and references therein.
21. Hamman, S.; Benaissa, T.; Beguin, C. G. J. Chem. Res., Miniprint 1992, 360-373.
22. Williams, R. M. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: 1995; Vol. 1, pp 45-94 and references therein.
23. Yuki, Y.; Saigo, K.; Tachibana, K.; Hasegava, M. Chem. Lett. 1986, 1347-1350.
24. (a) Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299-305.
25. (b) Brown, B.; Hegedus, L. S. J. Org. Chem. 1998, 63, 8012-8018.
26. Solladié-Cavallo, A.; Lupattelli, P.; Marsol, C.; Isarno, T.; Bonini, C.; Caruso, L.; Maiorella, A. Eur. J. Org. Chem. 2002, 1439-1444.
27. Lupattelli, P.; Bonini, C.; Caruso, L.; Gambacorta, A. J. Org. Chem. 2003, 68, 3360-3363.
28. Changes in reagent concentration had no apparent effect on the reaction.
29. At -30°C with LiBr/substr. 4/1 and Amb 15/substr. 220 mg/mmol, we had syn/anti = 20/80; see ref 14.
30. Akgün, E.; Glinski, M. B.; Dhawan, K. L.; Durst, T. J. Org. Chem. 1981, 46, 2730-2734.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
32. Each structure was confirmed as a real minimum by noting the absence of imaginary values in the list of length frequencies.
33. For a recent study on the electronic effect on the regioselectivity in the opening of aryloxiranes with acetylides, see: Shindo, M.; Sugioka, T.; Shishido, K. Tetrahedron Lett. 2004, 9265-9268.
34. Imuta, M.; Ziffer, H. J. Org. Chem. 1979, 44, 2505-2509.
35. Majima, T.; Tojo, S.; Ispida, A.; Takamuko, S. J. Org. Chem. 1996, 61, 7793-7800.