The N,N,N′,N′-tetramethylethylenediamine mediated Baylis-Hillman reaction

Synthetic Communications

Volumn 35, Issue 1, 2005, Pages 121-127

  Zhao, Sanhu ^a   Chen, Zhaobin ^a  

^a SHANXI UNIVERSITY   (China)

Author keywords

Baylis Hillman reaction; Catalyze; N,N,N N Tetramethylethylenediamine

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ACRYLIC ACID BUTYL ESTER; ALDEHYDE; ALKENE; N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; PUTRESCINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; REACTION ANALYSIS; STOICHIOMETRY;

EID: 13944284442     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200046521     Document Type: Article

References (17)

1. Basaviah, D.; Rao, A. J.; Satyanarayana, T. Recent advances in the Baylis-Hillman reaction and applications. Chem. Rev. 2003, 103, 811-891.
2. Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron 1996, 52, 8001-8062.
3. Drewes, S. E.; Roos, G. H.P. Synthetic potential of the tertiary-amine-catalysed reaction of activated vinyl carbanions with aldehydes. Tetrahedron 1988, 44, 4653-4670.
4. Rezgui, F.; El Gaied, M. M. DMAP-catalyzed hydroxymethylation of 2-cyclohexenones in aqueous medium through Baylis-Hillman reaction. Tetrahedron Lett. 1998, 39, 5965-5966.
5. Aggarwal, V. K.; Mereu, A. Superior amine catalysts for the Baylis-Hillman reaction: the use of DBU and its implication. Chem. Commun. 1999, 2311-2312.
6. Basavaiah, D.; Krishnamacharyulu, M.; Jaganmohan Rao, A. The aqueous trimethylamine mediated Baylis-Hillman reation. Synth. Commun. 2000, 30, 2061-2069.
7. Langer, P. New strategies for the development of an asymmetric version of the Baylis-Hillman reaction. Angew. Chem. Int. Ed. 2000, 39, 3049-3052.
8. Rauhut, M. M.; Currier, H. U.S. Patent 3 074 999, 1963 (American Cyanamide Co.), Chem. Abstr. 1963, 58, 11224a.
9. Yamada, Y. M. A.; Ikegami, S. Efficient Baylis-Hillman reactions promoted by cooperative catalysts and their application to catalytic asymmetric synthesis. Tetrahedron Lett. 2000, 41, 2165-2169.
10. Kataoka, T.; Iwama, T.; Tsujiyama, S.-i.; Iwamura, T.; Watanabe, S.-i. The chalcogeno-Baylis-Hillman reaction: A new preparation of allylic alcohods form aldehydes and electron-deficient alkenes. Tetrahedron 1998, 54, 11813-11824.
11. Taniguchi, M.; Hino, T.; Kishi, Y. Aldol reaction of allenolates generated via 1,4-addition of iodide anion or its equivalent to α,β-acetylenic ketones. Tetrahedron Lett. 1986, 27, 4767-4770.
12. Baylis, A. B.; Hillman, M. E. D. German Patent 2 155 113, 1972; Chem. Abstr. 1972, 77, 34174q.
13. Coelho, F.; Almeida, W. P.; Veronese, D.; Mateus, C. R.; Silva Lopes, E. C.; Rossi, R. C.; Silveira, G. P.C.; Pavam, C. H. Ultrasound in Baylis-Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations. Tetrahedron 2002, 58, 7437-7447.
14. Yu, C.; Liu, B.; Hu, L. Efficient Baylis-Hillman reaction using stoichiometric base catalyst and an aqueous medium. J. Org. Chem. 2001, 66, 5413-5418.
15. Yu, C.; Hu, L. Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes. J. Org. Chem. 2002, 67, 219-223.
16. Lee, K. Y.; Kim, J. M.; Kim, J. N. Synthesis of 3-substituted-4- hydroxyquinoline N-oxides from the Baylis-Hillman adducts of O-nitrobenzaldehydes. Tetrahedron 2003, 59, 385-390.
17. Souza, R. O. M. A.; Meireles, B. A.; Aguiar, L. C. S.; Vasconcellos, M. L. A. A. Hexamethylenetetramine as a cheap and convenient alternative catalyst in the Baylis-Hillman reaction: Synthesis of aromatic compounds with anti-malarial activity. Synthesis 2004, 10, 1595-1600.