Wiest, Johannes M.; Conner, Michael L.; Brown, M. Kevin published the artcile< Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates>, Application In Synthesis of 277306-29-3, the main research area is hebelophyllene E sesquiterpene lactone preparation relative configuration; alkene catalytic enantioselective cycloaddition allenoate; chiral geminal dimethylcyclobutane derivatives preparation diastereoselective reduction; oxazaborolidine catalyst enantioselective cycloaddition alkene allenoate; cycloaddition; enantioselectivity; natural products; small ring systems; total synthesis.
The first synthesis of hebelophyllene E (I) is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophyllene E. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and allenoates provides access to the required chiral geminal dimethylcyclobutanes. Key to its success is the identification of a novel oxazaborolidine catalyst which promotes the cycloaddition in high enantioselectivities with good functional-group tolerance (9 examples, up to 97:3 e.r.). Thus, a late-stage cycloaddition using a fully functionalized alkene, followed by a diastereoselective reduction allows a concise entry to this class of natural products.
Angewandte Chemie, International Edition published new progress about [2+2] Cycloaddition reaction (enantioselective, of alkenes and allenoates). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Application In Synthesis of 277306-29-3.
Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate