Temperature-independent stereocontrolled [2+2] cycloaddition. Potential of the 2,4-pentanediol tether in asymmetric reactions as a differential activation entropy promoter

Journal of the American Chemical Society

Volumn 122, Issue 9, 2000, Pages 2128-2129

  Sugimura, Takashi ^a   Tei, Takahiro ^a   Mori, Atsushi ^a   Okuyama, Tadashi ^a   Tai, Akira ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLACETONE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHIRALITY; ENTROPY; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0034620682     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993976o     Document Type: Article

References (41)

1. (a) Tai, A.; Kikukawa, T.; Sugimura, T.; Inoue, Y.; Abe, S.; Osawa, T.; Harada, T. Bull. Cliem. Soc. Jpn. 1994, 67, 2473-77.
2. (b) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohota, T.; Takaya, H.; Noyori, R. J. Am. Cliem. Soc. 1988,110, 629-631.
3. Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Cliem. Soc., Chein. Commun. 1988, 87-88.
4. (a) Sugimura, T.; Futagawa, T.; Tai, A. Tetrahedron Lett. 1988, 29, 5775-79.
5. Sugimura, T.; Futaaawa, T.; Yoshikawa, M.; Tai, A. Tetrahedron Lett. 1989, 30, 3807-10.
6. Sugimura, T.; Yoshikawa, M.; Futagawa, T.; Tai, A. Tetrahedron 1990,46,5955-66.
7. Sugimura, T.; Yoshikawa, M.; Mizuguchi, M.; Tai, A. Chem. Lett. 1999, 831-832,
8. (b) Underiner, T. L.; Paquette, L. A. J. Org. Chem. 1992, 57, 5438-46.
9. Sugimura, T.; Nishiyama, N.; Tai, A.; Hakushi, T. Tetrahedron: Asymmetry 1994,5, 1163-66.
10. Sugimura, T.; Iguchi, H.; Tsuchida, R.; Tai, A.; Nishiyama, N.; Hakushi, T. Tetrahedron: Asymmetry 1998, 9, 1007-13.
11. Sugimura, T.; Nishiyama, N.; Tai, A. Tetrahedron: Asymmetry 1993, 4,43-44.
12. Sugimura, T.; Yamada, H.; Inoue, S.; Tai, A. Tetrahedron: Asymmetry 1997, 8, 649-655.
13. Sugimura, T.; Inoue, S.; Tai, A. Tetrahedron Lett. 1998, 39, 6487-6490.
14. (e) Mori, A.; Sugimura, T.; Tai, A. Tetrahedron: Asymmetry 1997, 8, 661-664.
15. (f) Sugimura, T.; Nagano, S.; Tai, A. Chem. Lett. 1998, 45-46.
16. (g) Yamaguchi, K.; Sugimura, T.; Nishida, F.; Tai, A. Tetrahedron Lett. 1998, 39, 4521-24.
17. Since the latest mechanistic study of the Lewis acid promoted diastereodifferentiating nucleophilic addition to a PD acetal suggested an S-jllike mechanism, some of the reactions of PD acetals might also be classified into the group of PD tethered reactions. Sammakia, T.; Smith, R. S. J. Am. Chem. Soc. 1992, 114, 10998-10999.
18. For examples of the reactions using other bifunctional chiral auxiliaries as tethers, see: (a) Green, B. S.; Rabinsohn, Y.; Rejto, M. J. Chem. Soc., Chem. Commun. 1975, 313-314.
19. (b) Ukaji, Y.; Sada, K.; Inomata, K. Chem. Lett. 1993, 1227-1230.
20. Lipshutz, B. L.; Liu, Z.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567-5570.
21. Lipshutz, B. H.; Kayser, F.; Liu, Z. Angew. Chem., Int. Ed. Engl. 1994, 33, 1842-1844.
22. (e) Lipshutz, B. H.; James, B.; Vance, S.; Carrico, I. Tetrahedron Lett. 1997, 38, 753-756.
23. (f) Koide, N.; Hattori, T.; Miyano, S. Tetrahedron: Asymmetry 1994, 5, 1899-1994.
24. Eyring, H. J. Chem. Phys. 1935, 3, 107-115.
25. (a) Eliel, E. L. Stereoselectirity of Carbon Compounds; MacGrawHill: New York, 1962; pp 151-152, 237-239.
26. (b) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; pp 1-6.
27. Nogradi, M. Slereoselectwe Synthesis; VHC: Weinheim, 1995; pp 41-43.
28. Gawley, R. E. Principles of Asymmetric Synthesis; Pergamon: Oxford, 1996; pp 7-10.
29. For a review of [2+2] cycloaddition of ketenes, see: Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159-646.
30. For diastereodifferentiating [2+2] addition of ketene to olefin, see: (a) Granz, I.; Kunz, H. Synthesis 1994, 1353-58.
31. (b) Kanazawa, A.; Delair, P.; Pourashraf, M.; Greene, A. E. J. Chem. Soc., Perlon Trans, l 1997, 1911-21.
32. Cagnon, J. R.; Bideau, F. L.; Marchand-Brynaert, J.; Ghosez, L. Tetrahedron Lett. 1997, 38, 2291-2294.
33. For reviews of the Wolff rearrangement, see: (a) Meier, H.; Zeller, K. P.; Angew. Chem. 1975,87,52-61.
34. (b) Gill, G. B. In Comprehensive Organic Synthesis; Trost, B. M., Ed.: Pergamon: Oxford, 1991; Vol. 3, pp 887-912.
35. The stereochemical purities were determined by GLC equipped with FID or MS. Four more isomeric adducts, 1,2-trans-adducts and 2-keto-adducts, are possible besides 3. Analyses of the reaction mixtures and those after solvolysis indicated that formation of the isomers of 2 is below the detection limit (<0.5%) except for 3d and 3c. The de and isolated yield of 2 (and 3) were somewhat affected by the solvent used, photoirradiation time, and the irradiation wavelength. See the Supporting Information for the details.
36. The structure of the adduct 2a-c were fully identified. The stereochemistries of 2d and 3d were not determined. See the Supporting Information for the details.
37. The ketene generated through the base-promoted 1,2-elimination from a corresponding substrate also produced only 2a. See the Supporting Information for the details.
38. 3) at 300 K are only -15% for le and 27% for 1d. In 1e, stereodirections of ΔΔH‡ and ΔΔ5‡ are opposite, and thus, the result is also regarded as the stereoselectivity caused by ΔΔ5‡, which is reduced 12% by ΔΔH‡.
39. For reviews, see: (a) Winnik, M. A. Chem. Rev. 1981,81, 491-524.
40. (b) Nakagaki, R.; Sakuraai, H.; Murai, K. J. Phys. Org. Chem. 1989,2, 187-204.
41. If the conformational equilibration of the tether part is slower than the [2+2] addition, the de is also independent of the reaction temperature. This anti-Curtin-Hammett explanation also leads to the same conclusion that the chiral fate of the reaction is prearranged in the ground state. For kinetic data for intermolecular ketene [2+2] additions, see: Issacs, N. S.; Stanbury, P. 7. Chem. Soc., Perkin Trans. 2 1973, 166-169.