Modern Methods in Stereocontrolled Synthesis 1200-2SPEC102M

The lecture is aimed at presentation of basic concepts and modern methods of asymmetric organic synthesis.

The first part of the lecture will introduce fundamental concepts and definitions: chemoselectivity, regioselectivity, stereoselectivity, enantio- and diastereoselectivity. Next, methods for determination of enantiomeric and diastereoisomeric excess will be critically discussed. The next lectures will focus on additions of organometalic reagents to carbonyl group including thorough discussion of Cram and Felkin-Ankh models, with emphasis on broad applicability of Felkin-Ankh model in asymmetric synthesis. Following lectures will introduce methods for synthesis of chiral molecules with new stereogenic centers based on EPC synthesis, chiral auxiliary and chiral catalyst. These three methodologies of the stereoselective synthesis will be described using [4+2]cycloaddition (Diels-Alder reaction) and thoroughly illustrated with examples of total syntheses of natural products.
Next part of the lecture will be devoted to modern methods for the enantioselective alkynylation, alkenylation and arylation of carbonyl groups mediated by organozinc reagents. Diorganozinc-mediated reaction
can be highly advantageous in pharmaceutical applications.
In the last part of the lecture enantioselective Tsuji-Trost reaction, widely known as asymmetric allylic substitution, will be discussed. This process, being "dynamic kinetic asymmetric transformation" is a one of a few allowing for the transformation of a racemate into pure enantiomer with 100% chemical yield.

Lecture = 30 hours.
Individual preparation for each lecture (1.0 h weekly) = 15 hours.
Preparation for the exam = 25 hours.
Together = approximately 70 hours.

Main fields of studies for MISMaP

chemistry

Type of course

elective courses

Mode

Classroom

Prerequisites (description)

A student is supposed to have the knowledge of advanced organic chemistry required for the entrance examination for II degree studies in Chemistry at the Faculty of Chemistry, University of Warsaw.

Course coordinators

Tomasz Bauer

Learning outcomes

After completing the lecture, a student:
a) should be able to choose best method for determination of enantioselectivity
b) should be able to build a stereochemical model for simple enantio- and diastereoselective reactions
c) have a basic knowledge about most important methods for the stereogenic center generation.

Assessment criteria

Maximum amount of excused absence is 30%. Final examination with open-ended questions. Writing time 90 minutes. 60% (60/100 points) is required to pass the exam.

Practical placement

not applicable

Bibliography

Leading journals in organic chemistry

Additional information

Additional information (registration calendar, class conductors, localization and schedules of classes), might be available in the USOSweb system:

Description of 1200-2SPEC102M in USOSweb