β-Lactam synthesis by diastereoselective condensation of chiral 3-(p- tolylsulfinyl)-2-furaldimine and ester enolates

Heterocycles

Volumn 53, Issue 7, 2000, Pages 1479-1483

  Arai, Yoshitsugu ^b   Yoneda, Shinya ^a   Masuda, Tsutomu ^a   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 (PARA TOLYLSULFINYL) 2 FURALDIMINE; ESTER; IMINE; LACTAM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CRYSTAL; DRUG SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0034235617     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-00-8913     Document Type: Article

References (49)

1. I. Ojima, S. Inaba, and K. Yoshida, Tetrahedron Lett., 1977, 3643; E. W. Colvin, D. McGarry, and M. J. Nugent, Tetrahedron, 1988, 44, 4157; K. Hirai, H. Homma, and I. Mikoshiba, Heterocycles, 1994, 38, 281.
2. I. Ojima, S. Inaba, and K. Yoshida, Tetrahedron Lett., 1977, 3643; E. W. Colvin, D. McGarry, and M. J. Nugent, Tetrahedron, 1988, 44, 4157; K. Hirai, H. Homma, and I. Mikoshiba, Heterocycles, 1994, 38, 281.
3. I. Ojima, S. Inaba, and K. Yoshida, Tetrahedron Lett., 1977, 3643; E. W. Colvin, D. McGarry, and M. J. Nugent, Tetrahedron, 1988, 44, 4157; K. Hirai, H. Homma, and I. Mikoshiba, Heterocycles, 1994, 38, 281.
4. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
5. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
6. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
7. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
8. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
9. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
10. G. Guanti, E. Narisano, and L. Banfi, Tetrahedron Lett., 1987, 28, 4331, 4335; T. Mukaiyama, K. Kashiwagi, and S. Matsui, Chem. Lett., 1989, 1397; T. Mukaiyama, H. Akamatsu, and J. S. Han, Chem. Lett., 1990, 889; M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141; K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963; S. Kobayashi and S. Nagayama, Synlett, 1997, 653; J. Am. Chem. Soc., 1997, 119, 10049.
11. For reviews, see: D. J. Hart and D-C. Ha, Chem. Rev., 1989, 89, 1447; M. J. Brown, Heterocycles, 1989, 29, 2225; F. H. van der Steen and G. van Koten, Tetrahedron, 1991, 47, 7503.
12. For reviews, see: D. J. Hart and D-C. Ha, Chem. Rev., 1989, 89, 1447; M. J. Brown, Heterocycles, 1989, 29, 2225; F. H. van der Steen and G. van Koten, Tetrahedron, 1991, 47, 7503.
13. For reviews, see: D. J. Hart and D-C. Ha, Chem. Rev., 1989, 89, 1447; M. J. Brown, Heterocycles, 1989, 29, 2225; F. H. van der Steen and G. van Koten, Tetrahedron, 1991, 47, 7503.
14. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
15. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
16. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
17. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
18. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
19. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
20. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
21. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
22. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
23. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
24. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
25. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
26. I. Ojima and S. Inaba, Tetrahedron Lett., 1980, 21, 2077, 2081; H. Kunz and D. Schanzenbach, Angew. Chem., Int. Ed. Engl., 1989, 28, 1068; I. Ojima and I. Habus, Tetrahedron Lett., 1990, 31, 4289; T. Fujisawa, Y. Ukaji, T. Noro, K. Date, and M. Shimizu, Tetrahedron Lett., 1991, 32, 7563; H. Fujioka, T. Yamanaka, T. Matsunaga, M. Fuji, and Y. Kita, Synlett, 1992, 35; F. A. Davis, P. Zhou, and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; Y. Matsumura and T. Tomita, Tetrahedron Lett., 1994, 35, 3737; M. Shimizu, K. Kume, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 5227; M. Shimizu, K. Kume, and T. Fujisawa, Chem. Lett., 1996, 545; R. Annunziata, M. Cinquini, F. Cozzi, V. Molteni, and O. Schupp, Tetrahedron, 1996, 52, 2573; M. Panunzio, R. Camerini, R. Pachera, D. Donati, C. Marchioro, and A. Perboni, Tetrahedron:Asymmetry, 1996, 7, 2929; H. Fujieda, M. Kanai, T. Kambara, A. Iida, and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; K. Higashiyama, H. Kyo, and H. Takahashi, Synlett, 1998, 489.
27. C. Gennari, I. Venturini, G. Gislon, and G. Schimperna, Tetrahedron Lett., 1987, 28, 227; G. I. Georg, J. Kant, and H. S. Gill, J. Am. Chem. Soc., 1987, 109, 1129; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud, and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; M. Shimizu, Y. Teramoto, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729.
28. C. Gennari, I. Venturini, G. Gislon, and G. Schimperna, Tetrahedron Lett., 1987, 28, 227; G. I. Georg, J. Kant, and H. S. Gill, J. Am. Chem. Soc., 1987, 109, 1129; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud, and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; M. Shimizu, Y. Teramoto, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729.
29. C. Gennari, I. Venturini, G. Gislon, and G. Schimperna, Tetrahedron Lett., 1987, 28, 227; G. I. Georg, J. Kant, and H. S. Gill, J. Am. Chem. Soc., 1987, 109, 1129; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud, and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; M. Shimizu, Y. Teramoto, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729.
30. C. Gennari, I. Venturini, G. Gislon, and G. Schimperna, Tetrahedron Lett., 1987, 28, 227; G. I. Georg, J. Kant, and H. S. Gill, J. Am. Chem. Soc., 1987, 109, 1129; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud, and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; M. Shimizu, Y. Teramoto, and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729.
31. K. Ishihara, M. Miyata, K. Hattori, T. Tada, and H. Yamamoto, J. Am. Chem. Soc., 1994, 116, 10520; H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 1997, 119, 7153.
32. K. Ishihara, M. Miyata, K. Hattori, T. Tada, and H. Yamamoto, J. Am. Chem. Soc., 1994, 116, 10520; H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 1997, 119, 7153.
33. Y. Arai, T. Masuda, and Y. Masaki, Synlett, 1997, 1459.
34. 3 are reported to be ineffective for the reaction of silyl ketene acetals with sulfinimines: R. Kawecki, J. Org. Chem., 1999, 64, 8724.
35. 2O affords best results as solvent. T. Mukaiyama, H. Suzuki, and T. Yamada, Chem. Lett., 1986, 915.
36. R. Annunziata, M. Cinquini, F. Cozzi, and P. G. Cozzi, J. Org. Chem., 1992, 57, 4155; T. Fujisawa, R. Hayakawa, and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; T. Fujisawa, K. Higuchi, and M. Shimizu, Synlett, 1993, 59; R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, and V. Molteni, Tetrahedron, 1996, 52, 2583.
37. R. Annunziata, M. Cinquini, F. Cozzi, and P. G. Cozzi, J. Org. Chem., 1992, 57, 4155; T. Fujisawa, R. Hayakawa, and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; T. Fujisawa, K. Higuchi, and M. Shimizu, Synlett, 1993, 59; R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, and V. Molteni, Tetrahedron, 1996, 52, 2583.
38. R. Annunziata, M. Cinquini, F. Cozzi, and P. G. Cozzi, J. Org. Chem., 1992, 57, 4155; T. Fujisawa, R. Hayakawa, and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; T. Fujisawa, K. Higuchi, and M. Shimizu, Synlett, 1993, 59; R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, and V. Molteni, Tetrahedron, 1996, 52, 2583.
39. R. Annunziata, M. Cinquini, F. Cozzi, and P. G. Cozzi, J. Org. Chem., 1992, 57, 4155; T. Fujisawa, R. Hayakawa, and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; T. Fujisawa, K. Higuchi, and M. Shimizu, Synlett, 1993, 59; R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, O. Martini, and V. Molteni, Tetrahedron, 1996, 52, 2583.
40. Predominant formation of β-lactams would reflect that the ring closure reaction proceeds at a greater rate on the geminal (i.e. dimethyl) substitution: P. D. Bartlett, J. Chem. Educ., 1953, 30, 22; T. C. Bruice and U. K. Pandit, J. Am. Chem. Soc., 1960, 82, 5858. Hydrolysis of 7 and subsequent esterfication gave 4, thus confirming the assignment of structure (4).
41. Predominant formation of β-lactams would reflect that the ring closure reaction proceeds at a greater rate on the geminal (i.e. dimethyl) substitution: P. D. Bartlett, J. Chem. Educ., 1953, 30, 22; T. C. Bruice and U. K. Pandit, J. Am. Chem. Soc., 1960, 82, 5858. Hydrolysis of 7 and subsequent esterfication gave 4, thus confirming the assignment of structure (4).
42. For example, see: P. Andreoli, G. Cainelli, M. Contento, D. Giacomini, G. Martelli, and M. Panunzio, J. Chem. Soc., Perkin Trans. I, 1988, 945.
43. 3).
44. Stereochemical assignments are by analogy with the results obtained with 2 and 6.
45. 2O and/or in the presence of HMPA, β-amino esters were also produced in variable yield. Judging from preliminary experiments in the presence of HMPA, the ratio of syn-and anti-esters was reversed, affording the anti-β-amino esters preferentially. For example, a report of the reversal in diastereoselection in HMPA - THF, see: T. Chiba, M. Nagatsuma, and T. Nakai, Chem. Lett., 1984, 1927.
46. K. Hattori and H. Yamamoto, Tetrahedron, 1994, 50, 3099.
47. H. E. Zimmerman and M. D. Traxler, J. Am. Chem. Soc., 1957, 79, 1920. For example, S. R. Chemler and W. R. Roush, Tetrahedron Lett., 1999, 4643; R. A. Batey, A. N. Thadani, and D. V. Smil, Tetrahedron Lett., 1999, 4289.
48. H. E. Zimmerman and M. D. Traxler, J. Am. Chem. Soc., 1957, 79, 1920. For example, S. R. Chemler and W. R. Roush, Tetrahedron Lett., 1999, 4643; R. A. Batey, A. N. Thadani, and D. V. Smil, Tetrahedron Lett., 1999, 4289.
49. H. E. Zimmerman and M. D. Traxler, J. Am. Chem. Soc., 1957, 79, 1920. For example, S. R. Chemler and W. R. Roush, Tetrahedron Lett., 1999, 4643; R. A. Batey, A. N. Thadani, and D. V. Smil, Tetrahedron Lett., 1999, 4289.