Date of Award
© 2017 Sooyun Choi. All rights reserved. This work is freely available courtesy of the author. It may only be used for non-commercial, educational, and research purposes. For all other uses, including reproduction and distribution, please contact the copyright holder.
Bachelor of Arts
Chemistry & Biochemistry
Robert S. Paley
Organoiron complexes have established their utility in organic synthesis as stereodirecting groups as well as diene protecting groups. Since its first discovery in 1930, the diene tricarbonyl iron(O) complex underwent an impressive development that allows us to use its rich chemistry to accomplish complex molecule synthesis and to explore various synthetic methods that would broaden the scope of this field. The Paley laboratory utilizes the planar chirality of N-oxazolidinoyl diene tricarbonyl iron complexes to expand the boundaries of diastereoselective synthesis of novel compounds. The findings reported here reflect our attempts not only to reiterate the successful chemistry previously done on the p-tolyl sulfoxide diene tricarbonyl iron(O) complexes on the recently investigated N-oxazolidinoyl diene iron(O) complexes, but also to further explore possible transformations of the complexes. The synthetic goals of this thesis work included various diastereoselective reactions: 1,4 conjugate additions to the alkylidene malonate analog of the title compound, allylation of cyclic oxocarbenium ion on the periphery of the diene, intramolecular ring formation via Rh(II)-catalyzed C-H insertion and the Pictet- Spengler condensation. The first three reactions are shown to be diastereoselective, and an elaborate precursor to the Pictet-Spengler reaction is being pursued.
Choi, Sooyun , '17, "Diastereoselective Transformations and Intramolecular Cyclizations of Enantiomerically Pure Planar Chiral N-Oxazolidinoyl Diene lron(O) Tricarbonyl Complexes" (2017). Senior Theses, Projects, and Awards. 225.