Enantioselective synthesis of 4-alkenoic acids via Pd-catalyzed allylic alkylation: stereocontrolled construction of γ and δ-lactones

• Published in: Tetrahedron: asymmetry Vol. 26; no. 15-16; pp. 802 - 809
• Main Authors: Alvarado-Beltrán, Isabel, Maerten, Eddy, Toscano, R. Alfredo, López-Cortés, José G., Baceiredo, Antoine, Álvarez-Toledano, Cecilio
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 31-08-2015; Elsevier
• Subjects: Catalysis; Chemical Sciences; Organic chemistry
• ISSN: 0957-4166; 1362-511X; 0957-4166
• DOI: 10.1016/j.tetasy.2015.06.003

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An enantioselective and diastereoselective synthesis of γ,δ-unsaturated carboxylic acids by palladium-catalyzed carbon alkylation of bis(trimethylsilyl)ketene acetals with (E)-1,3-diphenylpropenyl acetate was developed. These acids could be efficiently turned into new γ- or δ-halolactones containing multiple stereocenters using a halolactonization protocol. The stereochemistry of these acids was established by X-ray analysis after derivatization to the corresponding amide with (R)-(+)-1-phenylethylamine.