Facile Lewis Acid-Mediated Ring Opening of 4-Hydroxypyrrolidin-2-ones by Amino Acid Esters

Synlett

Volumn 1996, Issue 5, 1996, Pages 479-480

  Rotella, David P ^a  

^a CEPHALON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001802323     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5456     Document Type: Article

References (14)

1. Fehrentz, J. A.; Bourdel, E.; Califano, J. C.; Chaloin, O.; Devin, C.; Garrouste, P.; Lima-Leite, A. C.; Llinares, M.; Rieunier, F.; Vizavonna, J.; Wintemitz, F.; Loffet, A.; Martinez, J. Tet. Lett. 1994, 35, 1557.
2. a) Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles 1992, 33, 1051-78;
3. b) Abdel-Meguid, S. Med. Res. Review 1993, 13, 731.
4. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc. Perkin Trans. 1 1987, 1177.
5. Klutchko, S.; O'Brien, P.; Hodges, J.C. Syn. Comm. 1989, 19, 2573.
6. Andrew, R. G.; Conrow, R. E.; Elliott, J. D.; Johnson, W. S.; Ramezani, S. Tet. Lett. 1987, 28, 6535.
7. Ojima, I.; Sun, C. M.; Park, Y. M. J. Org. Chem. 1994, 59, 1249.
8. N-carboxy anhydrides are available from SNPE/Propeptide, Princeton, NJ.
9. Bon, E.; Bigg, D. C. H.; Bertrand, G. J. Org. Chem. 1994, 59, 1904.
10. 3, δ): 0.91, d, 6H, J=6.5 Hz; 1.24-1.39, m, 1H; 1.41, s, 9H; 1.44, s, 9H; 1.48-1.80, m, 2H, 2.26-2.40, m, 2H, 3.08, d, 2H, J=5.8 Hz, 3.54-3.60, m, 1H, 3.93-3.97, m, 1H, 4.69-4.76, m, 1H, 6.29, d, 1H, J=7.5 Hz.
11. 3) for entries a, d f and g from Table 1: entry a: 0.91, d, 6H, J=6.5 Hz; 1.36, d, 3H, J=6.9 Hz; 1.44, s, 9H; 1.46, s, 9H; 1.50-1.70, m, 3H; 2.37-2.42, m, 2H; 3.53-3.68, m, 1H; 3.96-4.02, m, 1H; 4.40-4.48, m, 1H; 4.86, d, 1H, J=9.7 Hz; 6.76, d, 1H, J=7.1 Hz; entry d: 0.90-0.98, m, 12H; 1.22-1.43, m, 2H; 1.43, s, 9H, 1.48, s, 9H; 1.50-1.72, m, 4H; 2.38-2.42, m, 2H, 3.63-3.72, m, 1H; 3.93-4.00, m, 1H; 4.38-4.48, m, 1H, 4.89, d, 1H, J=9.6 Hz; 6.80, d, 1H, J=7.2 Hz; entry f: 0.89-0.97, m, 12H; 1.30-1.40, m, 1H; 1.43, s, 9H; 1.49, s, 9H; 1.50-1.70, m, 2H; 2.10-2.20, m, 1H; 2.40-2.50, m, 2H; 3.60-3.70, m, 1H; 3.95-4.02, m, 1H; 4.40-4.47, m, 1H; 4.83, d, 1H, J=9.7 Hz; 6.62, d, 1H, J=7.1 Hz; entry g: 0.88, app. t, 6H, J=3 Hz; 1.21-1.34, m, 1H; 1.38, s, 9H; 1.42, s, 9H; 1.56-1.60, m, 2H; 2.16-2.34, m, 2H; 3.17-3.38, m, 2H; 3.42-3.60, m, 1H; 4.77-4.86, m, 2H; 6.61, d, 1H, J=7.7 Hz; 7.0, s, 1H; 7.11, app. t, 1H, J=7.1 Hz; 7.16, app. t, 1H, J=7.8 Hz; 7.33, d, 1H, J=8 Hz; 7.56, d, 1H, J=7.7 Hz; 8.57, s, 1H.
12. Basha, A.; Lipton, M.; Weinreb, S.M. Tet. Lett. 1977, 18, 4171.
13. Fehrentz, J. A.; Genu-Dellac, C.; Amblard, M.; Winternitz, F.; Loffet, A.; Martinez, J.; J. Peptide Sci. 1995, 1, 124.
14. Galeotti, N.; Poncet, J.; Chiche, L.; Jouin, P. J. Org. Chem. 1994, 59, 5370.