Lithium perchlorate-accelerated Baylis-Hillman reactions

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1539-1542

  Kawamura, Mikako ^a,b   Kobayashi, Shu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ALDEHYDE; CARBONYL DERIVATIVE; ETHER DERIVATIVE; LITHIUM; PERCHLORATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION;

EID: 0033582768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02705-1     Document Type: Article

References (12)

1. (a) Baylis, A. B.; Hillma, M. E. D. German Patent 2155113 (1972); Chem. Abstr. 1972, 77, 34174q.
2. (b) Morita, K.; Suzuki, Z.; Hirose, H. Bull. Chem. Soc. Jpn. 1968, 41, 2815.
3. (a) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
4. (b) Fort, Y.; Berthe, M. C. Tetrahedron 1992, 48, 6371.
5. (c) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653.
6. Cf. (a) Imagawa, T.; Uemura, K.; Nagai, Z.; Kawanishi, M. Synth. Commun. 1984, 14, 1267.
7. (b) Kataoka, T.; Iwama, T.; Tsujiyama, S. J. Chem. Soc., Chem. Commun. 1998, 197.
8. 4. Mukaiyama, T.; Kobayashi, S.; Shoda, S. Chem. Lett. 1984, 907.
9. Recently, Aggarwal et al. reported that lanthanide triflates accelerate the Baylis-Hillman reaction. Aggarwal, V. K.; Tarver, G. J.; McCague, R. J. Chem. Soc., Chem. Commun. 1996, 2713.
10. 4. (a) Grieco, P. A.; Nunes, J. J.; Gaul, M. D. J. Am. Chem. Soc. 1990, 112, 4595.
11. (b) Grieco, P. A.; Clark, J. D.; Jagoe, C. T. J. Am. Chem. Soc. 1991, 113, 5488.
12. The yield was further improved when 15 mol% of DABCO was used. See Table 1.