Topic outline

  • All contact sessions will take place in Zoom: https://aalto.zoom.us/j/65148800304


    My idea of the course...

    The selective assembly of molecular structures regarding positions or relative configurations of functional groups represents a crucial skill in modern organic synthesis, and a prerequisite in the production of fine chemicals, pharmaceuticals and agrochemicals.

    This course takes up previously reviewed organic transformations and discusses them in the context of regio- and diastereoselectivity. The Selectivity course will provide the tools to perform conformational analyses and employ general concepts such as polarity control and orbital control to predict reaction outcomes and relative configurations in C-C and C-heteroatom bond forming transformations. Reactions will include the addition of simple carbon nucleophiles, enolates and P-, S-, and Si-stabilized carbanions to carbonyls and olefinic double bonds as well as cycloadditions and rearrangements.   


    How does it work...

    We will have 9 lecture-type sessions, complemented by 6 exercise discussions because none of the stuff we'll be talking about will very easily stick. It needs to be applied!

    You will find my slides prior to the lectures on this page, and that's also where I will post the video recordings after the sessions.

    You will find me in Zoom. Even though all videos will also be made available, please join me for our contact sessions: https://aalto.zoom.us/j/65148800304


    What is expected from you...

    We are likely gonna be a small bunch, so please make full use of that situation and try to be active. You will get most out of the course if you ask the questions whenever I may be too vague with my explanations or if you feel uncertain. Stereochemistry comes natural to some of us but may need hard training for others, and whatever type you are, I will do my best to make it work for you.

    There will be two things that are compulsory to pass the course.

    1. To hand in 3 sets of home assignments. Those are different from (but similar to) the exercises that we discuss in the contact sessions. You probably want to solve them by pen-and-paper and upload a scan/photograph, but we can discuss that once we meet. Those account for 45% of the points that go into the final grade.

    2. To have a nice chat with me after the course in which we talk about the stereochemistry. Well, it is officially called an oral examination but really nothing to be bothered with. If you engage in the discussions and hand in your assignments, you will also be comfortable talking some chemistry with me. The oral examinations (duration: 30 min) are scheduled for April 15th (afternoon), and will account for 55% of the final grade.


    Preliminary outline 

    2.3.2021: Stereoelectronics & sterics

    5.3.2021:     ---Exercise #1---

    9.3.2021: Diastereoselectivity in cyclic systems 

    10.3.2021: Diastereoselectivity in acyclic systems (only as video recording!)

    12.3.2021:     ---Exercise #2---

    16.3.2021: Simple diastereoselectivity

    17.3.2021: Aldol additions

    19.3.2021:     ---Exercise #3---

    23.3.2021: Addition to olefins

    24.3.2021: Synthesis of olefins

    26.3.2021:     no contact session 

    30.3.2021:    ---Exercise #4---

    31.3.2021: Cycloadditions

    6.4.2021:     ---Exercise #5---

    7.4.2021: Sigmatropic rearrangements (only as video recording!)

    9.4.2021:     ---Exercise #6---