Studies towards total synthesis of antillatoxin: Investigation of the indium-mediated allylation reactions of carbonyl compounds with β-bromocrotylbromide in water

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1453-1456

  Loh, Teck Peng ^a   Cao, Guo Qiang ^a   Pei, Jian ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM CHLORIDE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; INDIUM; LANTHANIDE; TOXIN; WATER;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; STEREOCHEMISTRY; TOXIN SYNTHESIS; ULTRASOUND;

EID: 0032510461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10826-7     Document Type: Article

References (18)

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2. 2. For the synthesis of aldehyde 3, refer to Loh, T.-P.; Cao, G.-Q.; Jian, P.; submitted for publication.
3. 3. The allylation reactions of compounds using allyl halides and In in aqueous media were previously reported: (a) Li, C. J.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 7017.
4. (b) Oda, Y.; Matsuo, S.; Saito, K. Tetrahedron Lett. 1992, 33, 97.
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9. (f) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500; see also Casiraghi, G.; Rassu, G. Chemtracts-Org. Chem, 1993, 6, 336.
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11. (h) Wang, R. B.; Lim, C. M.; Tan, C. H.; Lim, B. K.; Sim, K. Y.; Loh, T. P. Tetrahedron Asy. 1995, 6, 1825.
12. 4. Li, C. J. Chem. Rev. 1993, 93, 2023.
13. 5. Lanthanide triflate has been shown to increase the rate and selectivity of indium-mediated allylation reaction of carbonyl compounds (a) Wang, R-B.; Lim, C.-M.; Tan, C.-H.; Lim, B.-K.; Sim, K-Y.; Loh, T.-P. Tetrahedron: Asymmetry, 1995, 6, 1825-1828.
14. (b) Ho, Diana, S.-C.; Sim K.-Y. and Loh, T.-P. Synlett, 1996, 263-264.
15. (c) Loh, T.-P.; Wang R.-B.; Tan K. -L. and Sim K.-Y. Main Group Metal Chemistry, 1997, 20, 237-240.
16. (d) Loh, T.-P ; Cao, G.-Q unpublished results.
17. 6. Isaac, M. B.; Chan, T.-H. Tetrahedron Lett., 1995, 36, 8957-8960.
18. 7. This research was assisted financially by the National University of Singapore (RP 940633, RP950609, RP970615 and RP970616).