Effect of allylic CH3-nFn groups (n = 1-3) on π-facial diastereoselection

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2915-2918

  Yamazaki, Takashi ^a   Ichige, Tatsuro ^a   Takei, Satoshi ^a   Kawashita, Seiji ^a   Kitazume, Tomoya ^a   Kubota, Toshio ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001032858     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016401g     Document Type: Article

References (31)

1. Gung, B. W.; le Noble, B. Guest editors for the special thematic issue on diastereoselection. Chem. Rev. 1999, 99, 1067.
2. (a) Yamazaki, T.; Umetani, H.; Kitazume, T. Isr. J. Chem. 1999, 39, 193.
3. (b) Yamazaki, T.; Shinohara, N.; Kitazume, T.; Sato, S. J. Fluorine Chem. 1999, 97, 91.
4. (c) Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asymmetry 1997, 8, 1157.
5. Yamazaki, T.; Shinohara, N.; Kituzume, T.; Sato, S. J. Org. Chem. 1995, 60, 8140.
6. The independent reaction demonstrated that the E,Z ratio of 2 was 92:8 in favor of the E isomer. Details will be published elsewhere.
7. Overman, L. E.; Renaldo, A. F. J. Am. Chem. Soc. 1990, 112, 3945.
8. (a) MacPhee, J. A.; Panaye, A. Dubois, J.-E. Tetrahedron 1978, 34, 3553.
9. (b) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry Kodansha, Gordon, and Breach Science Publisher: Tokyo, 1998; Chapter 1. See also: Béguin, C. G.; Schlosser, M. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V., Ed.; John Wiley and Sons: New York, 1999; pp 601 and 613, respectively.
10. (b) Kitazume, T.; Yamazaki, T. Experimental Methods in Organic Fluorine Chemistry Kodansha, Gordon, and Breach Science Publisher: Tokyo, 1998; Chapter 1. See also: Béguin, C. G.; Schlosser, M. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds; Soloshonok, V., Ed.; John Wiley and Sons: New York, 1999; pp 601 and 613, respectively.
11. For the discussion of the number of fluorines and stereoselectivity, see: Soloshonok, V. A.; Kacharov, A. D.; Avilov, D. V.; Ishikawa, K.; Nagashima, N.; Hayashi, T. J. Org. Chem. 1997, 62, 3470.
12. O'Hagan, D. J. Fluorine Chem. 1989, 43, 371.
13. Lanier, M.; Haddach, M.; Pastor, R.; Riess, J. G. Tetrahedron Lett. 1993, 34, 2469 and references therein.
14. 2 was required just prior to use for reproducible results.
15. Fuchikami, T.; Shibata, Y.; Suzuki, Y. Tetrahedron Lett. 1986, 27, 3173.
16. Recently preparation of 3,3-difluoroacrylate was reported; see: Botteghi, C.; Paganelli, S.; Sbrogiò, F.; Zarantonello, C. Tetrahedron Lett. 1999, 40, 8435 and references therein.
17. Ando, K. J. Org. Chem. 1999, 64, 8406.
18. 19F NMR) while the minor isomer was removed after hydrolysis.
19. n-attached carbon in 6 is conveniently fixed as S for the simpler stereochemical discussion despite employment of their racemic forms except for the case of E-6a.
20. This donor was selected because no 1,4-or 1,2-adducts were provided when ethyl propionate was used.
21. Gaussian 98, Revision A.7; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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.; Baboul, A. G.; 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, Inc.; Pittsburgh, PA, 1998.
22. Crystallographic data for the major diastereomer of 13c has been deposited at the Cambridge Crystallographic Data Center and allocated the deposition number CCDC 166764.
23. Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132.
24. In the case of nonfluorinated systems, the Felkin-Anh model tor the E-acceptors and the 1,3-allylic strain concept for the Z-acceptors have been successfully employed for the explanation of the product stereochemistry; see, Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191.
25. Cieplak, A. S. Chem. Rev. 1999, 99, 1265.
26. Cieplak, A. S. J. Am. Chem. Soc. 1981, 103, 4540.
27. (a) Wong, S. S.; Paddon-Row: M. N.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1990, 112, 8679.
28. (b) Tatsukawa, A.; Kawatake, K.; Kanemasa, S.; Rudzinski, J. M. J. Chem. Soc., Perkin Trans. 1 1994, 2525. See also: Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029.
29. (b) Tatsukawa, A.; Kawatake, K.; Kanemasa, S.; Rudzinski, J. M. J. Chem. Soc., Perkin Trans. 1 1994, 2525. See also: Bernardi, A.; Capelli, A. M.; Cassinari, A.; Comotti, A.; Gennari, C.; Scolastico, C. J. Org. Chem. 1992, 57, 7029.
30. Seeman, J. I. Chem. Rev. 1983, 83, 83.
31. One reviewer suggested that Li⋯F chelation is also applicable tor the explanation of the present results, but this was ruled out here because of our previous experience on diastereoselectivity independent from the number of fluorines; see: Yamazaki, T.; Ando, M.; Kitazume, T.; Kubota, T.; Omura, M. Org. Lett. 1999, 1, 905.