The chalcogeno-Baylis-Hillman reaction of an α,β-unsaturated thioester: A new approach to α-methylene-β-hydroxy carboxylic acid derivatives

Synlett

Volumn , Issue 2, 1999, Pages 197-198

  Kataoka, T ^a   Iwama, T ^a   Kinoshita, H ^a   Tsujiyama, S ^a   Tsurukami, Y ^a   Iwamura, T ^a   Watanabe, S ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Chalcogeno Baylis Hillman reaction; , unsaturated thioester; methylene hydroxy thioester; methylene hydroxy ester

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALKENE; BENZALDEHYDE; CARBENE; CARBOXYLIC ACID; ESTER; HYDROXY FATTY ACID; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION;

EID: 0032909793     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2591     Document Type: Article

References (14)

1. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001; Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653; Ciganek, E. Org. React. 1997, 51, 201-350.
2. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001; Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653; Ciganek, E. Org. React. 1997, 51, 201-350.
3. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001; Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653; Ciganek, E. Org. React. 1997, 51, 201-350.
4. Brown, J. M.; Cutting, I. Chem. Commun. 1985, 578; Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
5. Brown, J. M.; Cutting, I. Chem. Commun. 1985, 578; Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317.
6. Atkinson, R. S.; Fawcett, J.; Russel, D. R.; Williams, P. J. Chem. Commun. 1997, 2031.
7. Bailey, M.; Markó, I. E.; Ollis, W. D. Tetrahedron Lett. 1991, 32, 2687.
8. Markó, I. E.; Giles, P. R.; Janousek, Z.; Hindley, N. J.; Declercq, J.-P.; Tinant, B.; Feneau-Dupont, J.; Svendsen, J. S. Recl. Trav. Chim. Pays-Bas 1995, 114, 239.
9. Kataoka, T.; Iwama, T.; Tsujiyama, S. Chem. Commun. 1998, 197; Kataoka, T.; Iwama, T.; Tsujiyama, S.; Iwamura, T.; Watanabe, S. Tetrahedron 1998, 54, 11813-11824.
10. Kataoka, T.; Iwama, T.; Tsujiyama, S. Chem. Commun. 1998, 197; Kataoka, T.; Iwama, T.; Tsujiyama, S.; Iwamura, T.; Watanabe, S. Tetrahedron 1998, 54, 11813-11824.
11. 4) and evaporated under reduced pressure. The residue was purified by preparative TLC on silica gel eluting with ethyl acet-ate-hexane (1:3, v/v).
12. 4S: C, 53.92; H, 4.90; N, 5.24. Found: C, 53.79; H, 4.91; N, 5.17.
13. 5: C, 58.86; H, 5.70; N, 5.28. Found: C, 58.71; H, 5.76; N, 5.25.
14. 1H NMR spectrum of the inseparable mixture suggested existence of ethanethiol-added products such as 12 and 13; however, we could not characterize the structure because of the complicated spectrum. (Matrix presented)