Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• the alkoxytriphenylphosphonium intermediate. Several reactions of the products were investigated to show the utility of the rearrangement. Keywords: bicyclic ring; cyrene; levoglucosenone; rearrangement; thionyl chloride; Introduction The 6,8-dioxabicyclo[3.2.1]octane derivative levoglucosenone (1

• levoglucosenone, cyrene and their derivatives, generating a unique set of bicyclic building blocks. Previous work on migration reactions in 6,8-dioxabicyclooctan-4-ols [18]. Mechanism for the rearrangement of 10, and Newman projection and the X-ray structure of 10d projected along the C4–C5 axis. Structures for

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• Dihydrolevoglucosenone (DLG) is prepared by hydrogenation of levoglucosenone in the presence of palladium as a catalyst. Recently, Debsharma et al. reported the CROP of levoglucosenyl alkyl ether in CH2Cl2 at 0 °C and at room temperature using triflic acid or boron trifluoride etherate as initiators [46][47][48]. The 1H

Oxa-Michael-initiated cascade reactions of levoglucosenone

• Julian Klepp,
• Thomas Bousfield,
• Hugh Cummins,
• Sarah V. A.-M. Legendre,
• Jason E. Camp and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2022, 18, 1457–1462, doi:10.3762/bjoc.18.151

• , United Kingdom 10.3762/bjoc.18.151 Abstract The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate

• chemistry; levoglucosenone; oxa-Michael reaction; Introduction (−)-Levoglucosenone (1) is formed from the acid-catalyzed pyrolysis of cellulose along with minor amounts of furfural and 5-methylfurfural [1][2][3]. It has emerged as a promising starting material for enantioselective synthesis from materials

• approximate 90° dihedral angle. Conclusion This work has described a novel reaction of a cyclic biomass-derived α,β-unsaturated ketone with aromatic aldehydes. The ready availability of levoglucosenone in large quantities from biomass could make compounds such as 5 of interest for green chiral materials

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

• an element of stereocontrol in highly selective chemical transformations has been widely explored [9]. In this context, as part of our continuous interest in the development of new tools for asymmetric synthesis using levoglucosenone (a biomass-derived chiral enone) [10][11][12][13][14][15], we

• auxiliary. Results and Discussion The synthesis of acrylate derivatives 6a,b bearing CF3 and OMe substituents in the para position of the phenoxy group is depicted in Scheme 1. Levoglucosenone (1) was used as a dienophile to react with the corresponding 9-substituted anthracenes 2a,b, which are easily

• aromatic rings. This can be useful in several fields, such as supramolecular chemistry, biology and material science and, in particular, in the area of asymmetric synthesis for the rational design of new elements of stereocontrol. Intramolecular aryl–vinyl π-stacking interaction of a levoglucosenone