Pyrrolidine-catalyzed homo-aldol condensation reactions of aldehydes

Synlett

Volumn , Issue 4, 1999, Pages 450-452

  Ishikawa, Teruhiko ^a   Uedo, Eiji ^a   Okada, Siho ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Homo aldol condensation; Pyrrolidine catalysis; Reverse Michael addition; , unsaturated aldehyde

Indexed keywords

ALDEHYDE; BENZOIC ACID; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; POLYMERIZATION;

EID: 0032945520     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2647     Document Type: Article

References (16)

1. Ramachandran, S.; Newman, M. S. Org. Synth., Coll. Vol. V 1973, 486; see also Hajos, Z. G.; Parrish, D. R. Org. Synth., Coll. Vol. VII 1990, 363 and Buchschacher, P.; Fürst, A.; Gutzwiller, J. Org. Synth., Coll. Vol. VII 1990, 368.
2. Ramachandran, S.; Newman, M. S. Org. Synth., Coll. Vol. V 1973, 486; see also Hajos, Z. G.; Parrish, D. R. Org. Synth., Coll. Vol. VII 1990, 363 and Buchschacher, P.; Fürst, A.; Gutzwiller, J. Org. Synth., Coll. Vol. VII 1990, 368.
3. Ramachandran, S.; Newman, M. S. Org. Synth., Coll. Vol. V 1973, 486; see also Hajos, Z. G.; Parrish, D. R. Org. Synth., Coll. Vol. VII 1990, 363 and Buchschacher, P.; Fürst, A.; Gutzwiller, J. Org. Synth., Coll. Vol. VII 1990, 368.
4. Wieland, P.; Miescher, K. Helv. Cheim. Acta 1950, 33, 2215.
5. Offenhauer, R. D.; Nelsen, S. F. J. Org. Chem. 1968, 33, 775.
6. Pfister, J. R. Tetrahedron Lett. 1980, 21, 1281.
7. 2OAc) and determined to be E. When the reaction was carried out at elevated temperature, E → Z isomerization took place to a significant extent probably through Michael addition and its reverse process.
8. For this discussion, see Haynes, L. W. In Enamines: Synthesis, Structure, and Reactions; Cook, A. G. Ed.; Marcel Dekker: New York, 1969; p 55.
9. Elguero, J.; Jacquier, R.; Tarrago, G. Tetrahedron Lett. 1965, 4719: see also Malhotra, S. K.; Johnson, F. ibid. 1965, 4027.
10. Elguero, J.; Jacquier, R.; Tarrago, G. Tetrahedron Lett. 1965, 4719: see also Malhotra, S. K.; Johnson, F. ibid. 1965, 4027.
11. Takazawa, O.; Kogami, K.; Hayashi, K. Bull. Chem. Soc. Jpn. 1985, 58, 2427.
12. A very careful experiment to detect aldol-type products by tlc monitoring of the reaction has revealed that even a trace amount of product of this class was not produced.
13. For reverse Michael addition of β-pyrrolidinoesters or β-N,N-dimethylaminoesters, see (a) Berchtold, G. A.; Ciabattoni, J.; Tunick, A. A. J. Org. Chem. 1965, 30, 3679 and
14. (b) Danishefsky, S.; Cunningham, R. J. Org. Chem. 1965, 30, 3676, respectively.
15. No benzoic acid was added in this case because, when added, the reaction gave a complicated product mixture as recognized by tlc analysis.
16. NMR experiments exhibited hemiaminal carbon signal at 79 ppm and no enamine-based olefinic carbon and proton signals.