Stereoselective synthesis of functionalized carbocycles by cycloaddition to levoglucosenone

Mechanistic Insights into Water-Catalyzed Formation of Levoglucosenone from Anhydrosugar Intermediates by Means of High-Level Theoretical Procedures

“…Levoglucosenone (LGO) is one of the most valuable pyrolysis products due to its unique structure and functional groups (e.g., keto, olefinic, and ether groups) [7,8] . Accordingly, LGO is the starting material for a wide range of synthetic products including biologically active natural products, sugar mimetics, and agrochemicals [9,10] .…”

Levoglucosan and levoglucosenone as bio-based platforms for polymer synthesis

“…Shafizadeh et al 39 and Horton et al 40 first reported that LGO can act as a dienophile and undergo Diels–Alder cycloaddition with dienes, producing functionalised carbocycles. LGO itself does not directly undergo ring opening metathesis polymerization (ROMP), however the norbornene-LGO adduct possesses sufficient ring strain to successfully polymerize.…”

“…Shafizadeh et al 39 and Horton et al 40 first reported that LGO can act as a dienophile and undergo Diels-Alder cycloaddition with dienes, producing functionalised carbocycles.…”

Reactions of 3-iodolevoglucosenone with sodium derivatives of some CH acids. Chiral cyclopropanes and stable oxetenes

“…Mass spectra were recorded on an MX-1306 instrument (ionizing voltage 70 eV, temperature of the ionization chamber 30--50 *C). (7). Diethyl malonate (0.39 g, 2.4 retool) was added dropwise to a suspension of Nail (0.12 g, 4.8 retool) in 3 mL of THF, and the mixture was stirred for 30 rain.…”