Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1213-1216

  Baussanne, Isabelle ^a   Royer, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030038396     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02388-7     Document Type: Article

References (24)

1. Baussanne, I.; Chiaroni, A.; Husson, H.-P.; Riche, C.; Royer, J. Tetrahedron Lett. 1994, 35, 3931-3934.
2. a) For a recent review see: Cossy, J.; Vogel, P. In Studies in Natural Product Chemistry, Atta-ur-Rahman Ed., Elsevier: Amsterdam, 1993, 12, 275-363.
3. b) Hino, M.; Nakayama, O.; Tsurumi, Y.; Adachi, K. ; Shibata, T.; Terano, H.; Kohsaka, M.; Aoki, H.; Imanaka, H. The Journal of Antibiotics 1985, 926-935.
4. Ikota, N. Heterocycles 1993, 36, 2035-2050 and references therein.
5. a) Ohfune, Y.; Tomita, M. J. Am. Chem. Soc. 1982, 104, 3511-3513.
6. b) Johnston, G. A. R.; Curtis, M. R.; Davis, J.; Mc Culloch, R. M. Nature 1974, 248, 804.
7. c) Shinozaki, K. "Kainic Acid as a Tool in Neurobiology", Raven Press: N. Y., 1978.
8. d) Johnson, R. L.; Koener, J. F.; J. Med. Chem. 1988, 31, 2057-2066.
9. For a review see: Dai, W.-M.; Nagao, Y. Heterocycles 1990, 30, 1231-1261. and references therein.
10. Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1984, 49, 551-553.
11. a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
12. b) Casiraghi, G.; Spanu, P.; Rassu, G.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1994, 59, 2906-2909.
13. c) Rassu, G.; Zanardi, F.; Cornia, M.; Casiraghi, G.J. Chem. Soc. Perkin Trans. I, 1994, 2431-2437.
14. d) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760-3763.
15. e) Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L. Tetrahedron: Asymmetry 1992, 3, 1035-1048.
16. a) One example of a reaction between a chiral silyloxypyrrole and an achiral aldehyde has been reported in the literature: Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139-2140.
17. b) During the preparation of this manuscript, the synthesis (using our methodology) and reaction of a chiral silyloxypyrrole has been described: Poli, G.; Ciofi, S.; Maccagni, E.; Sardone, N. Tetrahedron Lett. 1995, 36, 8669-8672.
18. Aldol addition of acyclic chiral silyl ketene acetals has been extensively studied; see, for example, Gennari, C. in Comprehensive Organic Synthesis, Trost, B. M. Ed., Pergamon Press, 1991, vol 2, p 629-660
19. About 5% of the β, γ-unsaturated isomer was also formed in this reaction.
20. Prepared from (R)-(-)-phenylglycinol according to Meyers, A. I.; Poindexter, G. S.; Brich, Z. J. Org. Chem. 1978, 43, 892-898.
21. According to the l (like), u (unlike) nomenclature proposed by Seebach, D.; Prelog, V. Angew. Chem. Int. Ed. English 1982, 21, 654-660.
22. 3 at -78°C, gave a single observable compound (enantiomeric mixture): (equation presented)
23. 2O), 5.12 (dd, J=5.7, 8.7Hz, 1H, NCHPh), 6.15 (dd, J=6.0, 1.4Hz, 1H, H-3), 6.81 (dd, J=6.0, 1.6Hz, 1H, H-4), 7-7.4 (2m, 5H, ar.).
24. The X-ray crystallographic study was performed by A. Chiaroni and C. Riche at the Institut de Chimie des Substances Naturelles and will be reported separately.