Regioselective access to orthogonal Diels-Alder C60 bis-adducts and tris-heteroadducts via supramolecular mask strategy

Ring-Opening of Hetero-Diels--Alder Adducts

Thermally cleavable surfactants based on furan-maleimide Diels-Alder adducts.

Two new surfactant molecules are reported that contain thermally labile Diels-Alder adducts connecting the hydrophilic and hydrophobic sections of each molecule. The two surfactants possess identical hydrophobic dodecyl tail segments but have phenol and carboxylic acid hydrophilic headgroups, respectively. Deprotonation with potassium hydroxide affords the formation of water-soluble surfactants...

Synthesis of oxa-bridged derivatives from Diels–Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Bis-adducts of 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene and 1,3-butadiene, generated in situ from 3-sulfolene, have been synthesized in excellent yield. Ruthenium catalyzed oxidation of the bis-adducts followed by a one-pot transformation of the resulting alpha-diketone furnished oxa-bridged compounds. Unambiguous stereochemical assignments of both diastereomeric series are reported.

Diels-Alder cycloaddition strategy for kinetic resolution of chiral pyrazolidinones.

A rare example of the application of a catalytic, enantioselective Diels-Alder cycloaddition to affect a kinetic resolution has been developed. Chiral pyrazolidinones are resolved with high selectivity through a process that utilizes a relay of stereochemical information from a permanent chiral center to a fluxional chiral center to enhance the inherent selectivity of the chiral Lewis acid cata...

Enantioselective and regioselective pyrone Diels-Alder reactions of vinyl sulfones: total synthesis of (+)-cavicularin.

The total synthesis of (+)-cavicularin is described. The synthesis features an enantio- and regioselective pyrone Diels-Alder reaction of a vinyl sulfone to construct the cyclophane architecture of the natural product. The Diels-Alder substrate was prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene.