Irene Erdelmeier

Synthesis of optically active 3-oxa-carbacyclin precursors featuring asymmetric Horner-Emmons reaction

Abstract An enantioselective synthesis of 5 is described. Asymmetric Horner-Emmons reactions with the chiral phosphonate 6 are key steps in the synthesis of the allylic alcohols E - 8 and E - 11 from the ketones 5 and 9, respectively.

Stereoselective synthesis of enantiomerically pure 1-(E)-alkenylsulfoximines

Abstract Optically active (E)-N-tosyl-S-(1-alkenyl)-S-phenylsulfoximines 4 are synthesized stereoselectively in a one pot sequence from readily available 1 via C-silylation, metallation and reaction of the corresponding lithiosulfoximine 3 with various carbonyl compounds. The El-MS spectra of the so prepared alkenylsulfoximines 4 show unexpected fragmentations, pointing to a new, unusual S-O-migration of the 1-alkenyl moiety.