title: Cyclopentanoids by uncatalyzed intramolecular carbonyl ene (ICE) reaction of α-keto esters.
abstract: 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.
authors.affiliation: Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund , 44227 Dortmund, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Tymann
authors.forename: André
authors.initials: A
authors.lastname: Klüppel
authors.forename: Wolf
authors.initials: W
authors.lastname: Hiller
authors.forename: Martin
authors.initials: M
authors.lastname: Hiersemann
mesh_terms: D004952:Esters; D007659:Ketones / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007659:Ketones; D020005:Propanols; D012821:Silanes; C006463:allyl alcohol