This course builds on the material learned in Organic Chemistry I or Organic Chemistry II for Biology/Pharmacy Students. Topics include advanced concepts and mechanisms of organic reactions and introductions to pericyclic and organometallic reactions. These topics are combined to the planning and execution of multiple step syntheses of complex molecules.
Learning objective
Goals of this course include the a deeper understanding of basic organic reactions and mechanism as well as advanced and catalytic transformations (for example, Mitsunobu reactions, Corey-Chaykovsky epoxidation, Stetter reactions, etc). Reactive intermediates including carbenes and nitrenes are covered, along with methods for their generation and use in complex molecule synthesis. Frontier molecular orbital theory (FMO) is introduced and used to rationalize pericyclic reactions including Diels Alder reactions, cycloadditions, and rearrangements (Cope, Claisen). The basic concepts and key reactions of catalytic organometallic chemistry, which are key methods in modern organic synthesis, and introduced, with an emphasis on their catalytic cycles and elementrary steps. All of these topics are combined in an overview of strategies for complex molecule synthesis, with specific examples from natural product derived molecules used as medicines.
Content
Oxidation and reduction of organic compounds, redox netural reactions and rearrangments, advanced transformations of functional groups and reaction mechanismes, kinetic and thermodynamic control of organic reactions, carbenes and nitrenes, frontier molecular orbital theory (FMO), cycloadditions and pericyclic reactions, introduction to organometallic chemistry and catalytic cross couplings, introduction to peptide synthesis and protecting groups, retrosynthetic analysis of complex organic molecules, planning and execution of multi-step reaction.
Lecture notes
The lecture notes and additional documents including problem sets are available as PDF files online, without charge. Link: http://www.bode.ethz.ch/education.html
Literature
Clayden, Greeves, and Warren. Organic Chemistry, 2nd Edition. Oxford University Press, 2012.
