A highly diastereoselective and enantioselective Ti(OTos)2-TADDOLate-catalyzed 1,3-dipolar cycloaddition reaction of alkenes with nitrones

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 59-63

  Gothelf, Kurt V ^a   Thomsen, Ib ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002402464     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952726e     Document Type: Article

References (57)

1. Huisgen, R. Angew. Chem. 1963, 75, 604.
2. For general reviews see: (a) Padwa, A., Ed. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nirronates in Organic Synthesis; VCH: New York, 1988.
3. For general reviews see: (a) Padwa, A., Ed. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984. (b) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nirronates in Organic Synthesis; VCH: New York, 1988.
4. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
5. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
6. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
7. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
8. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
9. For recent 1,3-dipolar cycloaddition reactions with chiral nitrones, see: (a) Kiers, D.; Moffat, D.; Overton, K.; Tomanek, R. J. Chem. Soc., Perkin Trans. I 1991, 1041. (b) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1063. (c) Goti, A.; Cicchi, S.; Brandi, A.; Pitrusiewicz, K. M. Tetrahedron: Asymmetry 1991, 2, 1371. (d) McCraig, A. E.; Wightman, R. H. Tetrahedron Lett. 1993, 34, 3939. (e) Saito, S.; Ishikawa, T.; Kishimoto, N.; Kohara, T.; Moriwake, T. Synlett 1994, 282. (f) Oppolzer, W.; Deerberg, J.; Tamura, O, Helv. Chim. Acta 1994, 77, 554.
10. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
11. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
12. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
13. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
14. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
15. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
16. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
17. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
18. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
19. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
20. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
21. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
22. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
23. For recent 1,3-dipolar cycloaddition reactions with chiral alkenes, see: (a) Olsson, T.; Stern, K.; Westman, G.; Sundell, S. Tetrahedron 1990, 46, 2473. (b) Ito, M.; Kibayashi, C. Tetrahedron 1991, 47, 9329. (c) Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Chem. Commun. 1991, 117. (d) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T.; Shiro, M. Tetrahedron: Asymmetry 1991, 2, 1379. (e) Panfil, I.; Belzecki, C.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. Tetrahedron 1991, 47, 10087. (f) Krol, W. J.; Mao, S.; Steele, D. L.; Townsend, C. A. J Org. Chem. 1991, 56, 728. (g) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wisniewski, W J. Org. Chem. 1991, 56, 4382. (h) Annunziata, R.; Cinqumi, M.; Cozzi, F.; Giaroni, P.; Raimondi, L. Tetrahedron Let. 1991, 32, 1659. (i) Ito, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765. (j) Bravo, P.; Bruché, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli. A. Tetrahedron: Asymmetry 1993, 4, 2131. (k) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279. (I) Rispens, M. T.; Keller, E.; Lange, B.; Zijlstra, R. W. J.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 607. (m) Ina, H.; Ito, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun, 1995, 1015. (n) Langlois, N.; Bac, N. V.; Dahuron, N.; Delcroix, J.-M.; Devine, A.; Griffart-Brunet, D.; Chiaroni, A.; Riche, C. Tetrahedron 1995, 51, 3571.
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47. 21 The optical purities reported in this work are determined by HPLC with <2% deviations of the ee's.
48. 7b have described nitrone 2a with an E-geometry referring to Bravo et al. Tetrahedron: Asymmetry 1993, 4, 2131. Thus, we assume that the proposed stable E-geometry of 2a might be based on a misunderstanding.
49. 7b have described nitrone 2a with an E-geometry referring to Bravo et al. Tetrahedron: Asymmetry 1993, 4, 2131. Thus, we assume that the proposed stable E-geometry of 2a might be based on a misunderstanding.
50. 7b have described nitrone 2a with an E-geometry referring to Bravo et al. Tetrahedron: Asymmetry 1993, 4, 2131. Thus, we assume that the proposed stable E-geometry of 2a might be based on a misunderstanding.
51. 7b have described nitrone 2a with an E-geometry referring to Bravo et al. Tetrahedron: Asymmetry 1993, 4, 2131. Thus, we assume that the proposed stable E-geometry of 2a might be based on a misunderstanding.
52. 2a The face of 1a to which the nitrone approaches is the Re-face of the α-C atom in the α,β-unsaturated carbonyl moiety.
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