Piperonal as electrophile in the Baylis-Hillman reaction. A synthesis of hydroxy-β-piperonyl-γ-butyrolactone derivative

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8609-8612

  Almeida, Wanda P ^b   Coelho, Fernando ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b PAULISTA UNIVERSITY   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; GAMMA BUTYROLACTONE DERIVATIVE; LIGNAN;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; SYNTHESIS; ULTRASOUND;

EID: 0032547968     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01927-3     Document Type: Article

References (14)

1. 1 - For reviews, see, Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001, and Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
2. 1 - For reviews, see, Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001, and Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
3. 2 - a) Trost, B. M. Science 1983, 219, 245.
4. b) For examples of asymmetric Baylis-Hillman reaction, see: Leahy, J. W.; Rafel, S.; Brzezinski, L. J. J. Am. Chem. Soc. 1997, 119, 4317; Markó, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015; Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969, and references therein.
5. b) For examples of asymmetric Baylis-Hillman reaction, see: Leahy, J. W.; Rafel, S.; Brzezinski, L. J. J. Am. Chem. Soc. 1997, 119, 4317; Markó, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015; Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969, and references therein.
6. b) For examples of asymmetric Baylis-Hillman reaction, see: Leahy, J. W.; Rafel, S.; Brzezinski, L. J. J. Am. Chem. Soc. 1997, 119, 4317; Markó, I. E.; Giles, P. R.; Hindley, N. J. Tetrahedron 1997, 53, 1015; Gilbert, A.; Heritage, T. W.; Isaacs, N. S. Tetrahedron: Asymmetry 1991, 2, 969, and references therein.
7. 3 - For a recent review on lignans, neolignans and related compounds see Ward, R. S. Nat. Prod. Rep. 1997, 43.
8. 4 and then purified by column chromatography (silica gel 70-230 mesh, eluated with Hexane-ethyl acetate 80:20) to furnish the Baylis-Hillman adduct.
9. 5 - Forty, Y.; Berthe, M. C.; Caubere, P. Tetrahedron 1992, 48, 6371.
10. 6 - White, J. D.; Kuo, S.-C.; Vedananda, T. R. Tetrahedron Lett. 1987, 28, 3061.
11. 7 - This protocol allows an intramolecular hydrogen bonding for both diastereoisomers (equation presented)
12. AB for the minor isomer is 7.8Hz, suggesting anti configuration. Heathcock, C. H., in Asymmetric Synthesis, Morrison, J. D., Ed., Academic Press, London, 1984, 3, Part B, 115.
13. 9 - Perlmutter, P.; Tabone, M. Tetrahedron Lett. 1988, 29, 949
14. 10 - Drewes, S.E.; Emslie, N. D.; Field, J. S.; Kahn, A. A; Ramesar, N. Tetrahedron: Asymmetry 1992, 3, 255.