301659-48-3Relevant academic research and scientific papers
Synthesis of α-allyloxy-substituted α,β-unsaturated esters via aldol condensation. Convenient access to highly substituted allyl vinyl ethers
Hiersemann
, p. 1279 - 1290 (2007/10/03)
α-Allyloxy-substituted α,β-unsaturated esters 1a-r have been prepared in 5 steps from commercially available starting materials. The key sequence of the synthesis is an aldol addition between an α-allyloxy-substituted ester 2a-i and an aldehyde R1CHO followed by mesylation and DBU mediated elimination to afford the 2-alkoxycarbonyl-substituted allyl vinyl ethers 1a-r. The E/Z ratio of the newly generated vinyl ether double bond is apparently determined by the steric bulk of the vinyl ether double bond substituent R1. Z:E ratios from 3:2-9:1 were obtained.
