SubjectsSubjects(version: 855)
Course, academic year 2019/2020
  
Stereoselective Organic Syntheses - N110035
Title: Stereoselektivní organické syntézy
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2013
Semester: winter
Points: winter s.:4
E-Credits: winter s.:4
Examination process: winter s.:
Hours per week, examination: winter s.:2/1 C+Ex [hours/week]
Capacity: 30 / 30 (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
Level:  
For type:  
Guarantor: Hodačová Jana doc. Dr. Ing.
Annotation -
Last update: Hodačová Jana doc. Dr. Ing. (07.08.2013)
The course Stereoselective Organic Syntheses follows up to the courses of Organic Synthesis and Retrosynthesis. The aim of this course is to teach students the synthetic methods that allow them to control stereochemical course of organic reactions. The course includes basic organic stereochemistry, physico-chemical aspects of stereochemical transformations, and analytical methods applicable in the studies of chiral compounds. The students will be acquainted with a series of common stereoselective organic reactions. They should learn how to plan a synthetic strategy in order to obtain the desired stereoizomer of a product.
Aim of the course -
Last update: Cibulka Radek prof. Ing. Ph.D. (19.08.2013)

Students will be able to:

do stereochemical analysis of organic compounds and their reactions.

propose a suitable synthetic method for the preparation of the desired stereoizomer of a product.

prepare chiral non-racemic compound and determine its enantiomerical purity.

Literature -
Last update: Hodačová Jana doc. Dr. Ing. (07.08.2013)

R: Eliel, E. L.; Wilen, S. H.: Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994. ISBN 978-0-471-01670-0.

R: Atkinson, R. S.: Stereoselective Synthesis, Wiley, Chichester, 1995. ISBN 978-0-471-95419-4.

A: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E.: Stereoselective Synthesis v serii Methods of Organic Chemistry, Houben-Weyl, Vol. 21a-21f, 4. vydání, Thieme, Stuttgart, 1995. ISBN 9783131001146.

Learning resources -
Last update: Hodačová Jana doc. Dr. Ing. (06.08.2013)

A teacher will provide the study materials related to the lectures.

Requirements to the exam - Czech
Last update: Hodačová Jana doc. Dr. Ing. (30.08.2012)

Předmět je zakončen zápočtem a zkouškou.

Zápočet je udělen na základě aktivní účasti studenta na seminářích. Během semestru se píší dva testy (v 6. a 13. týdnu). K získání zápočtu musí student v každém z testů získat nejméně 50 bodů ze 100 možných.

Ke zkoušce může student přistoupit po získání zápočtu. Zkouška se skládá z písemné a ústní části. Ústní část může student absolvovat pokud získá z písemné části nejméně 50 bodů ze 100 možných.

Syllabus -
Last update: Hodačová Jana doc. Dr. Ing. (07.08.2013)

1. Chirality. Determination of the absolute configuration (CIP rules).

2. Stereochemical analysis. Stereochemical terminology.

3. Stereotransformations: physico-chemical description, examples.

4. Analytical methods for studies of chiral compounds and stereotransformations.

5. Methods of obtaining enantiomers.

6. Principles of stereoselective syntheses. Asymmetric induction.

7. Relative stereochemistry control. Cyclic tranzition state or cyclic intermediate.

8. Enantioselective reactions - a strategy based on chirality of a stoichimetric reagent.

9. Enantioselective reactions - a strategy based on chirality of a substrate.

10. Enantioselective catalysis - a formation of the C-O and C-N bond.

11. Enantioselective catalysis - a formation of the C-H and C-C bond.

12. Enantioselective organocatalysis.

13. Dynamic kinetic resolution. Enzymes in enantioselective syntheses.

14. Strategy of stereoselective syntheses. Examples of industrial applications.

Registration requirements -
Last update: Hodačová Jana doc. Dr. Ing. (06.08.2013)

Organic Synthesis

Retrosynthesis

Teaching methods
Activity Credits Hours
Účast na přednáškách 1 28
Příprava na přednášky, semináře, laboratoře, exkurzi nebo praxi 1,5 42
Příprava na zkoušku a její absolvování 1 28
Účast na seminářích 0,5 14
4 / 4 112 / 112
Coursework assessment
Form Significance
Examination test 50
Continuous assessment of study performance and course -credit tests 20
Oral examination 30

 
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