Synthesis of α-Allyloxy-Substituted α,β-Unsaturated Esters via Aldol Condensation. Convenient Access of Highly Substituted Allyl Vinyl Ethers
- 31 December 2000
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 2000 (09) , 1279-1290
- https://doi.org/10.1055/s-2000-6424
Abstract
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 esters 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.Keywords
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