Cyanomethylenetrimethylphosphorane, a powerful reagent for the Wittig olefination of esters, lactones and imides

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 235-237

  Tsunoda, Tetsuto ^a   Takagi, Harue ^a   Takaba, Daiki ^a   Kaku, Hiroto ^a   Itô, Shô ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Enol ethers; Esters; Imides; Lactones; Nitriles; Phosphoranes; Wittig reactions

Indexed keywords

ESTER; IMIDE; LACTONE; NITRILE; PHOSPHORANE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034620209     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02054-7     Document Type: Article

References (6)

1. Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., et al., Eds. Alkene synthesis. Pergamon Press: Tokyo, 1991; Vol. 1, 755-782.
2. Murphy, P. J.; Brennan, J. Chem. Soc. Rev. 1988, 17, 1-30.
3. Lakhrissi, M.; Chapleur, Y. Angew. Chem., Int. Ed. Engl. 1996, 35, 750-752.
4. Sabitha, G.; Reddy, M. M.; Srinivas, D.; Yadov, J. S. Tetrahedron Lett. 1999, 40, 165-166.
5. Tsunoda, T.; Nagino, C.; Oguri, M.; Itô, S. Tetrahedron Lett. 1996, 37, 2459-2462, and references cited therein.
6. Experimental conditions: CMMP (2.0-4.0 mmol) was added to a dry toluene solution (5 mL) of an ester (1 mmol) with stirring under argon atmosphere. For the reactions at a higher temperature, the mixture of the reactants was heated in an Ace pressure tube (Ace Glass Inc., max. 200 psi), after careful manipulation under argon atmosphere. After completion of the reaction, the solvent was evaporated in vacuo and the product was purified by silica gel column chromatography. The configuration at the double bond was assigned on the basis of the chemical shifts and/or NOESY NMR experiments.