Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 8/26/1999
Publication Date: N/A
Technical Abstract: The E-isomer selectivity of the Horner-Wadsworth-Emmons olefination of aldehydes has been improved by using Lithium tert- butoxide as the base, triethyl-2-phosphonopropionate or triethyl- 2-phosphonobutyrate as the phosphonate, and an aldehyde such as 2-methyl-2-pentenal, with hexane as the reaction solvent. Greater E-isomer selectivity was observed in the formation of 2- methyldienoates than 2-ethyldienoates. Application to the synthesis of sap-beetle aggregation pheromones will be discussed.