A New Two Steps Synthesis of α-Substituted γ-Methyl γ-Lactones from Nitroalkanes

Synlett

Volumn 1996, Issue 11, 1996, Pages 1115-1116

  Ballini, R ^a   Bosica, O ^a  

^a Dipto Scienze Chimiche dell'Univ   (Italy)

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Indexed keywords

EID: 0038235427     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5667     Document Type: Article

References (32)

1. Mori, K. Tetrahedron 1989, 45, 3233.
2. Dubs, P.; Stussi, R. Helv. Chim. Acta 1978, 61, 990.
3. Grimm, E. L.; Reissig, H.-U. J. Org. Chem. 1985, 50, 242 and references cited therein.
4. Ogliaruso, M. A.; Wolfe, J. F. Synthesis of Lactones and Lactams, Patai, S.; Rappoport, Z. Eds., John Wiley, Chichester, 1993.
5. Kano, S.; Shibuya, S.; Ebata, T. Heterocycles 1980, 14, 661.
6. Kobayashi, K.; Sasaki, A.; Kanno, Y.; Suginome, H. Tetrahedron 1991, 47, 7245.
7. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
8. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
9. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
10. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
11. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
12. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
13. For some recent approaches see: a) Black, T. W.; DuBay, W. J. Tetrahedron Lett. 1987, 28, 4787. b) Bunce, R. A.; Drumright, R. E.; Taylor, V. L. Synth. Commun. 1989, 19, 2423. c) Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J. Helv. Chim. Acta 1989, 72, 1362. d) Gutman, A. L.; Zuobi, K.; Bravdo, T. J. Org. Chem. 1990, 55, 3546. e) Frenette, R.; Monette, M.; Bernstein, M. A.; Young, R. N.; Verhoeven, T. R. J. Org. Chem. 1991, 56, 3083. f) Tamaru, Y.; Hogo, M.; Yoshida, Z. J. Org. Chem. 1991, 56, 1099. g) Sarmah, B. K.; Barua, N. C. Tetrahedron 1993, 49, 2253.
14. Zenk, P. C.; Wiley, R. A. Synthesis 1984, 695.
15. Black, T. H.; Fields, J. D. Synth. Commun. 1988, 18, 125.
16. Ferraz, H. M. C.; Ribeiro, C. M. R. Synth. Commun. 1992, 22, 399.
17. a) Seebach, D.; Colvin, E.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
18. b) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
19. c) Varma, R. S.; Kabalka, G. W. Heterocycles 1986, 24, 2645.
20. d) Fisher, R. H.; Weitz, H. M. Synthesis 1980, 261.
21. e) Ono, N.; Kaji, A. Synthesis 1986, 693.
22. a) Rosini, G.; Ballini, R. Synthesis 1988, 833.
23. b) Seebach, D.; Lehr, F. Angew. Chem. 1976, 88, 540.
24. c) Stach, H.; Hesse, M. Tetrahedron 1988, 44, 1573.
25. d) Rosini, G. in Comprehensive Organic Synthesis, Vol. 2 (Heathcock, C. H. Ed.) Chapt. 1.10 (p 321), Trost, B. M.; Fleming, I. Eds., Pergamon Press., Oxford, 1991.
26. e) Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213.
27. f) Ballini, R.; Marziali, P.; Mozzicafreddo, A. J. Org. Chem. 1996, 61, 3203 and references cited therein.
28. Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763.
29. 17
30. Kobayashi, Y.; Kishihara, K.; Watatani, K. Tetrahedron Lett. 1996, 37, 4385.
31. 3, 200 MHz): 1.26-1.62 (8H, m), 2.08-2.21 (2H, m), 2.2 (3H, s), 3.42 (2H, s), 3.65 (2H, t, J = 6.5Hz), 3.72 (3H, s), 7.0 (1H, t, J = 7.5Hz).
32. 3, 200 MHz): 1.2-2.1 (14H, m), 1.34 (0.6H, d, J = 6.4Hz), 1.38 (2.4H, d, J = 6.2Hz), 2.45-2.7 (1H, m), 3.62 (2H, t, J = 6.5Hz), 4.38-4.52 (0.8H, m), 4.58-4.72 (0.2H. m).