Application of the retroaldol reaction to asymmetric synthesis: A new concept in organic syntheses

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1015-1018

  Quesnel, Yannick ^a   Toupet, Loïc ^b   Duhamel, Lucette ^a   Duhamel, Pierre ^a   Poirier, Jean Marie ^a  

^a UNIVERSITÉ DE ROUEN   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE DERIVATIVE; BENZALDEHYDE; CARVONE; ORGANOLITHIUM COMPOUND; REAGENT;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ORGANIC CHEMISTRY; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033605668     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00093-2     Document Type: Article

References (22)

1. The directed aldol reaction, Mukaiyama, T. Organic Reactions; John Wiley: New York, 1982; Vol. 28, p. 204.
2. For uses of the retroaldol reaction in organic synthesis, see: (a) Ranu, B. C.; Basu, M. K. Tetrahedron Lett. 1991, 32, 4177. (b) Pak, C. S.; Kim, S. K.; Lee; H. K. Tetrahedron Lett. 1991, 32, 6011.
3. For uses of the retroaldol reaction in organic synthesis, see: (a) Ranu, B. C.; Basu, M. K. Tetrahedron Lett. 1991, 32, 4177. (b) Pak, C. S.; Kim, S. K.; Lee; H. K. Tetrahedron Lett. 1991, 32, 6011.
4. Philippini, M. H.; Rodriguez, J. J. Chem. Soc., Chem. Commun. 1995, 33.
5. Duhamel, P.; Cahard, D.; Quesnel, Y.; Poirier, J. M. J. Org. Chem. 1996, 61, 2232.
6. (e) Quesnel Y. Thesis; Rouen, 1997.
7. (a) Heathcock, C. H. In Asymmetric Synthesis; Morisson, J. D., Ed.; Acyclic stereoselection via the aldol condensation; Academic Press, 1984; Vol. 3, p. 111.
8. (b) Eliel, E. E. In ACS Symposium Series; Comstock, M. J., Ed.; Asymmetric reactions and processes in chemistry; Washington, 1982; p. 55.
9. Gaully, R. E.; Aubé, J. In Tetrahedron Organic Chemistry Series; Aldol and Michael additions of alkyls and enolates, principles of asymmetric synthesis; Elsevier, 1996; Vol. 14, p. 161.
10. 5a in THF (3 ml) was added potassium tert-butoxide (0.56 g, 5 mmol) in THF (2 ml) at -20°C. After 1 h, lithium bromide (1.74 g, 20 mmol) in THF (3 ml) was added and the reaction was stirred for 15 min. The mixture was cooled to -78°C and benzaldehyde (0.53 g, 5 mmol) in THE (3 ml) was added. After 5 h, water was added and the residue was purified by chromatography on silica gel leading to aldols 5a and 5b with a de >98% after one crystallisation from petroleum ether.
11. (a) Cazeau, P.; Moulines, F.; Laporte, O.; Duboudin, F. J. Organomet. Chem. 1980, 201, 2075.
12. (b) House, H. O. Rec. Chem. Prog. 1967, 28, 99.
13. Duhamel, P.; Cahard, D.; Poirier, J. M. J. Chem. Soc., Perkin Trans. 1 1993, 21, 2509.
14. (a) Vaillancourt, V.; Agharahimi, M. R.; Sundram, U. N.; Richou, O.; Faulkner, D. J.; Albizati, K. F. J. Org. Chem. 1991, 56, 378.
15. (b) Hutchinson, J. H.; Li, D. L. F.; Money, T.; Palme, M.; Agharahimi, M. R.; Albizati, K. F. Can. J. Chem. 1991, 69, 558.
16. 2: Calcd C, 79.03; H, 8.59; found: C, 78.44; H, 8.81.
17. (matrix presented)
18. Two diastereomers were detected by NMR. Their absolute configurations were not determined.
19. D=47.0 (c 2.2, hexane) see: (a) Pickard, R. A.; Fenyon, J. J. Chem. Soc. 1914, 1115. (b) Niwa, S.; Soai, K. J. J. Chem. Soc., Perkin Trans. 1 1991, 2717.
20. D=47.0 (c 2.2, hexane) see: (a) Pickard, R. A.; Fenyon, J. J. Chem. Soc. 1914, 1115. (b) Niwa, S.; Soai, K. J. J. Chem. Soc., Perkin Trans. 1 1991, 2717.
21. (a) Nakawaga, M.; Nakawanaga, T.; Kawate, T.; Kakikawa, T.; Yamada, H.; Matsui, T.; Hino, T. Tetrahedron 1993, 49, 1739.
22. (b) Jones, G. G.; Heaton, S. B. Tetrahedron: Asymmetry 1993, 4, 261.