Geminal bond participation and torquoselectivity in cheletropic reactions

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8509-8512

  Naruse, Yuji ^a   Hayashi, Yasuhiro ^a   Inagaki, Satoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METHYL GROUP; SILANE DERIVATIVE;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; MOLECULAR MODEL; PREDICTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; THEORETICAL MODEL;

EID: 0141887523     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.088     Document Type: Article

References (48)

1. Inagaki S., Ikeda H. J. Org. Chem. 63:1999;7820.
2. Ikeda H., Naruse Y., Inagaki S. Chem. Lett. 1999;364.
3. Ikeda H., Ushioda N., Inagaki S. Chem. Lett. 2001;166.
4. Ikeda H., Kato T., Inagaki S. Chem. Lett. 2001;270.
5. 5a See also: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2001, 124, 6840.
6. 5a See also: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2001, 124, 6840.
7. 5a See also: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2001, 124, 6840.
8. 7.
9. Houk stated that interaction between the σ-orbital of the breaking σ-bond and the π*-orbital of the substituent rotating inward is important for torquoselectivity.
10. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4693 For recent applications, see: Ma, J.; Inagaki, S. J. Phys. Chem. 2000, 104, 8989; Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193.
11. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4693 For recent applications, see: Ma, J.; Inagaki, S. J. Phys. Chem. 2000, 104, 8989; Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193.
12. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4693 For recent applications, see: Ma, J.; Inagaki, S. J. Phys. Chem. 2000, 104, 8989; Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193.
13. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4693 For recent applications, see: Ma, J.; Inagaki, S. J. Phys. Chem. 2000, 104, 8989; Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193.
14. Fukui, K.; Inagaki, S. J. Am. Chem. Soc. 1975, 97, 4445. Inagaki, S.; Fujimoto, H.; Fukui, K. J. Am. Chem. Soc. 1976, 98, 4693 For recent applications, see: Ma, J.; Inagaki, S. J. Phys. Chem. 2000, 104, 8989; Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193.
15. Part of this work was presented at the 32nd UCRS meeting, Gifu, Oct 2001, 2P20.
16. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
17. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
18. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
19. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
20. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
21. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
22. Recent work on cheletropic reactions: Unruh, G. R.; Birney, D. M. J. Am. Chem. Soc. 2003, 125, 8529 and references cited therein. For a general review: Imoto, M. Kagaku 1977, 32, 141; Imoto, M. Kagaku 1977, 32, 228; Mock, W. L. Org. Chem. 1977, 35, Pt 2, 141. Stereospecificity in cheletropic reactions, see: (a) Lamal, D. M.; McGregor, S. D. J. Am. Chem. Soc. 1966, 88, 1335; (b) Mock, W. L. J. Am. Chem. Soc. 1966, 88, 2857; (c) McGregor, S. D.; Lamal, D. M. J. Am. Chem. Soc. 1966, 88, 2858.
23. Yamabe and Minato noted geminal bond participation in the decomposition of diazetine to ethylene and nitrogen: Yamabe S., Minato T. J. Phys. Chem. A. 105:2001;7281.
24. 10 In fact, the activation energies for 3-cyclopentenone and 3-sulfolene reactions are 49.1 kcal/mol and 38.9 kcal/mol, respectively, at the B3LYP/6-31G* level (ZPE corrected).
25. GAUSSIAN98 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.
26. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
27. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
28. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
29. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
30. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
31. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
32. For the bond model analysis, see Ref. 1; (a) Iwase, K.; Inagaki, S. Bull. Chem. Soc. Jpn. 1996, 69, 2781; (b) Inagaki, S.; Yamamoto, T.; Ohashi, S. Chem. Lett. 1997, 977. See also: Refs. 2-4; (c) Inagaki, S.; Kawata, H.; Hirabayashi, Y. Bull. Chem. Soc. Jpn. 1982, 55, 3724; (d) Inagaki, S.; Goto, N. J. Am. Chem. Soc. 1987, 109, 3234; (e) Inagaki, S.; Goto, N.; Yoshikawa, K. J. Am. Chem. Soc. 1991, 113, 7144; (f) Inagaki, S.; Yoshikawa, K.; Hayano, Y. J. Am. Chem. Soc. 1993, 115, 3706; (g) Inagaki, S.; Ishitani, Y.; Kakefu, T. J. Am. Chem. Soc. 1994, 116, 5956.
33. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
34. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
35. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
36. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
37. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
38. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
39. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
40. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
41. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
42. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
43. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
44. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
45. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
46. ij are the elements of the density, Fock and core Hamiltonian matrices of the bond orbitals, respectively. (a) Inagaki, S.; Ohashi, S. Theo. Chem. Acc. 1999, 102, 65; (b) Inagaki, S.; Ohashi, S.; Kawashima, T. Org. Lett. 1999, 1, 1145-1147; (c) Inagaki, S.; Ikeda, H.; Kawashima, T. Tetrahedron Lett. 1999, 40, 8893; (d) Ma, J.; Inagaki, S. J. Phys. Chem. A 2000, 104, 8989; (d) Naruse, Y.; Hayashi, A.; Sou, S.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 245; (e) Ma, J.; Ikeda, H.; Inagaki, S. Bull. Chem. Soc. Jpn. 2001, 74, 273; (f) Ma, J.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 1193; (g) Ohwada, T.; Miura, M.; Tanaka, H.; Sakamoto, S.; Yamaguchi, K.; Ikeda, H.; Inagaki, S. J. Am. Chem. Soc. 2001, 123, 10164; (h) Naruse, Y.; Ma, J.; Inagaki, S. Tetrahedron Lett. 2001, 42, 6553; (i) Ikeda, H. ; Inagaki, S. J. Phys. Chem. A 2001, 105, 10711; (j) Ma, J.; Hozaki, A.; Inagaki, S. Inorg. Chem. 2002, 41, 1876; (k) Ma, J.; Hozaki, H.; Inagaki, S. Phosphorus, Sulfur and Silicon 2002, 177, 1705; (l) Naruse, Y.; Inagaki, S.; Kano, N.; Nakagawa, N.; Kawashima, T. Tetrahedron Lett. 2002, 43, 5759; (m) Naruse, Y.; Ma, J.; Inagaki, S. J. Phys. Chem. A 2003, 107, 2860; See also Refs. 2-4.
47. 17 Lee, P. S.; Zhang, X.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 5072.
48. For a review, see: Eliel E.L., Wilen S.H. Stereochemistry of Organic Compounds. 1994;695-700 John Wiley and Sons, New York.