Remarkable catalytic activity of Me3Ga in the alkylation of hetero- substituted epoxides with alkynyllithiums

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5881-5884

  Ooi, Takashi ^a   Morikawa, Junko ^a   Ichikawa, Hayato ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Alkylation; Epoxides; Gallium and Compounds; Lithium and Compounds

Indexed keywords

EPOXIDE; LITHIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; TRIMETHYLGALLIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0033529829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01096-5     Document Type: Article

References (6)

1. Ooi T, Kagoshima N, Ichikawa H, Maruoka K. J. Am. Chem. Soc. 1999;121:3328. See also: Ooi T, Kagoshima N, Maruoka K. J. Am. Chem. Soc. 1997;119:5754.
2. Ooi T, Kagoshima N, Ichikawa H, Maruoka K. J. Am. Chem. Soc. 1999;121:3328. See also: Ooi T, Kagoshima N, Maruoka K. J. Am. Chem. Soc. 1997;119:5754.
3. For a review of epoxide chemistry including ring opening, see: Gorzynski SJ. Synthesis 1984:629.
4. Utimoto K, Lambert C, Fukuda Y, Shiragami H, Nozaki H. Tetrahedron Lett. 1984;25:5423.
5. 3Ga (1 mol%) in THF at 20 °C for 5 h gave only a trace amount of 2, probably because of interference with the crucial chelate formation by the coordination of THF solvent to the gallium center. This result could also exclude the possibility that the ate complex might be an active species for the present alkynylation. See ref. 3.
6. The reaction conditions were not optimized.