Complete Reversal in Regioselectivity in the Baeyer-Villiger Reaction of an α-CF3-Ketone and Theoretical Rationale for Axial Orientation of Sterically Demanding CF3 Group at the Transition State

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4803-4806

  Itoh, Yoshimitsu ^a   Yamanaka, Masahiro ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; FUNCTIONAL GROUP; KETONE DERIVATIVE;

ARTICLE; BAEYER VILLIGER REACTION; DIPOLE; MOLECULAR INTERACTION; STEREOCHEMISTRY; THEORETICAL STUDY;

EID: 0347228975     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0358298     Document Type: Article

References (34)

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16. 2) in 89% yield.
17. 3-cyclohexanone.
18. 19F NMR of the reaction mixture showed 91% yield of 2-trifluoromethyl-6-hexanolide.
19. 5 (quantitative yield) gave the product.
20. Kotsuki, H.; Arimura, K.; Araki, T.; Shinohara, T. Synlett 1999, 462-464.
21. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
22. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
23. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
24. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
25. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
26. There are some theoretical studies of the B-V reaction: (a) Stoute, V. A.; Winnik, M. A.; Csizmadia, I. G. J. Am. Chem. Soc. 1974, 96, 6388-6393. (b) Hannachi, H.; Anoune, N.; Arnaud, C.; Lantéri, P.; Longeray, R.; Chermett, H. J. Mol. Struct. 1998, 434, 183-191. (c) Cádenas, R.; Reyes, L.; Lagúnez-Otero, J.; Cetina, R. J. Mol. Struct. 2000, 497, 211-225. (d) Cárdenas, R.; Cetina, R.; Lagúnez-Otero, J.; Reyes, L. J. Phys. Chem. 1997, 101, 192-200. (e) Okuno, Y. Chem. Eur. J. 1997, 3, 212-218. (f) Eklund, P. R.; Brinck, T. J. Org. Chem. 2001, 66, 1193-1199.
27. All calculations were performed using the Gaussian 98 program package (Gaussian, Inc.: Pittsburgh, PA, 1998).
28. Reference 14e was referred to in determining the calculation level. In reference 14e, the difference between HF/3-21G and MP2/6-31G* was examined in the case of the B-V reaction of formaldehyde by performic acid as the model study. The result of the structural difference was only 3%. Therefore, MP2/6-31G**//HF/6-31G* (higher level than HF/3-21G) was employed in this study.
29. Hehre, W. J.; Radom, L.; von Ragué Schleyer, P.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley: New York, 1986; see also references therein.
30. 3 group.
31. Length of H-F (2.06 Å) in CP1 is shorter than the sum of H and F van der Waals radii (2.60 Å).
32. (a) Curtin, D. Y. Rec. Chem. Prog. 1954, 15, 111-128.
33. (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 648 and references therein.
34. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, in press.