Alkylation of carbonyl compounds in the TiCl 4 -promoted reaction of trimethylsilyl enol ethers with ethylene oxide

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 763-766

  Lalic G ^a   Petrovski, Z ^a   Galonic D ^a   Matovic R ^a,b   Saicic R N ^a,b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b 11001   (Serbia)

Author keywords

Alkylation; Enolates; Epoxide; Titanium tetrachloride

Indexed keywords

CARBONYL DERIVATIVE; CHLORIDE; EPOXIDE; ETHER DERIVATIVE; ETHYLENE OXIDE; TITANIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL BOND; REACTION ANALYSIS; REPRODUCIBILITY;

EID: 0034728194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02149-8     Document Type: Article

References (18)

1. Reviews on the reactions of epoxides with nucleophiles: (a) with non-stabilized carbanions: Klunder, J. M.; Posner, G. H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp. 223-226;
2. (b) with vinyl carbanions: Knight, D. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp. 262-266;
3. (c) with alkynyl carbanions: Garratt, P. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp. 277-280.
4. (a) Carboxylic acid dianions: Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028-3030; Grieco, P. A.; Ohfune, Y.; Majetich, G. J. Org. Chem. 1979, 44, 3092; Iwai, K.; Kosugi, H.; Uda, H.; Kawai, M. Bull. Chem. Soc. Jpn. 1977, 50, 242-247
5. (a) Carboxylic acid dianions: Danishefsky, S.; Kitahara, T.; Schuda, P. F.; Etheredge, S. J. J. Am. Chem. Soc. 1976, 98, 3028-3030; Grieco, P. A.; Ohfune, Y.; Majetich, G. J. Org. Chem. 1979, 44, 3092; Iwai, K.; Kosugi, H.; Uda, H.; Kawai, M. Bull. Chem. Soc. Jpn. 1977, 50, 242-247
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7. (b) Amides: Hullot, P.; Cuvigny, T.; Larcheveque, M.; Normant, H. Can. J. Chem. 1977, 55, 266-273;
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9. Schreiber, S. L. J. Am. Chem. Soc. 1980, 102, 6163-6165.
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15. (c) Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043-1054.
16. For a review article on Ti-enolates see: Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 301-319.
17. Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341.
18. isobutane : 155 (M+1; 100%); 137 (M+1-18; 21%).