Stereoselective generation of cis-2-lithio-3-CF3-oxirane via CF3-substituted β-oxido carbenoids. Highly stereoselective synthesis of CF3-substituted tri- and tetrasubstituted oxiranes and tetrasubstituted alkenes

Tetrahedron

Volumn 59, Issue 49, 2003, Pages 9811-9823

  Shimizu, Masaki ^a   Fujimoto, Takuya ^a   Liu, Xinyu ^a   Minezaki, Hiroshi ^a   Hata, Takeshi ^a   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Carbenoids; Fluorine; Lithium; Oxirane; Trifluoromethyl

Indexed keywords

ALKENE DERIVATIVE; CARBENOID; ETHYLENE OXIDE DERIVATIVE; ORGANOLITHIUM COMPOUND;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0242558389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.098     Document Type: Article

References (60)

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31. 2O, MeSiCl, MeI, aldehyde, or ketone was reported to proceed with retention of configuration at the lithiated carbon. (a) Eisch J.J., Galle J.E. J. Organomet. Chem. 341:1988;293-313 (b) Molander G.A., Mautner K. J. Org. Chem. 54:1989;4042-4050 (c) Eisch J.J., Galle J.E. J. Org. Chem. 55:1990;4835-4840 (d) Lohse P., Loner H., Acklin P., Sternfeld F., Pfaltz A. Tetrahedron Lett. 32:1991;615-618 (e) Capriati V., Florio S., Luisi R., Salomone A. Org. Lett. 4:2002;2445-2448.
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