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Synthesis 2000; 2000(9): 1279-1290
DOI: 10.1055/s-2000-6424
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Synthesis of α-Allyloxy-Substituted α,β-Unsaturated Esters via Aldol Condensation. Convenient Access of Highly Substituted Allyl Vinyl Ethers

Martin Hiersemann*
  • *Institut für Organische Chemie der Technischen Universität Dresden, 01062 Dresden, Germany; Fax+ 49 35 14 63 70 30; E-mail: martin.hiersemann@chemie.tu-dresden.de
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Publication Date:
31 December 2000 (online)

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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.

allyl vinly ethers - aldol reactions - eliminations - esters