Cyclopentanoids by Uncatalyzed Intramolecular Carbonyl Ene (ICE) Reaction of α‑Keto Esters
journal contributionposted on 2014-08-15, 00:00 authored by David Tymann, André Klüppel, Wolf Hiller, Martin Hiersemann
The uncatalyzed intramolecular carbonyl ene (ICE) reaction of substituted ε,ζ-unsaturated α-keto esters to terpenoid-related building blocks has been studied. We found a beneficial effect of a silyl substituent at the ene segment on the kinetics of the ICE reaction. A generalizable and scalable synthesis of ε,ζ-unsaturated α-keto esters from allylic alcohols was developed.