Lead-Promoted 2-Carboethoxyallylation or 2-Carboxylallylation of Aldehydes: A New and Facile Method for the Synthesis of α-Methylene-γ-Butyrolactones
- 1 June 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (12) , 2397-2406
- https://doi.org/10.1080/00397919608004550
Abstract
In the presence of powdered lead, the reaction of aldehydes and α-bromomethylacrylate (or α-bromomethylacrylic acid) can be carried out under mild condition, the products 4-hydroxy-2-methylenebutanoates (or 4-hydroxy-2-methylenebutanoic acids) can be easily converted to α-methylene-γ-butyrolactones in the presence of CF3COOH.Keywords
This publication has 27 references indexed in Scilit:
- Tin- and indium-mediated allylation in aqueous media: application to unprotected carbohydratesThe Journal of Organic Chemistry, 1993
- Stereocontrolled synthesis of the hemibrevetoxin ring system via an allylic tin methodJournal of the Chemical Society, Chemical Communications, 1993
- Tin(II)-aluminum-promoted allylation of aldehydes with allyl chloride in an aqueous solvent systemThe Journal of Organic Chemistry, 1985
- Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagentsThe Journal of Organic Chemistry, 1984
- CARBON–CARBON BOND FORMATION WITH METALLIC MANGANESEChemistry Letters, 1983
- Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminumOrganometallics, 1983
- Samarium diiodide as coupling agent between aldehydes and organic halides for the synthesis of homoallylic and homobenzylic alcoholsTetrahedron Letters, 1982
- Oraganometallic Compounds for Stereoregulated Synthesis of Acyclic Systems. Their Application to the Synthesis of the Prelog-Djerassi Lactonic AcidHETEROCYCLES, 1982
- AN EFFICIENT SYNTHESIS OF HOMOALLYL ALCOHOLS BY THE REACTION OF ALLYL HALIDES WITH CARBONYL COMPOUNDS IN THE PRESENCE OF METALLIC TINChemistry Letters, 1981
- Ultrasounds in organic syntheses. 1. Effect on the formation of lithium organometallic reagentsJournal of the American Chemical Society, 1980