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Course, academic year 2023/2024

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Stereoselective Syntheses - M342011
Title: Stereoselektivní syntézy
Guaranteed by: Department of Chemistry of Natural Compounds (342)
Faculty: Faculty of Food and Biochemical Technology
Actual: from 2020
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 [HT]
Capacity: unlimited / unlimited (unknown)
Min. number of students: unlimited
State of the course: taught
Language: Czech
Teaching methods: full-time
Teaching methods: full-time
Note: course can be enrolled in outside the study plan
enabled for web enrollment
Guarantor: Parkan Kamil doc. Ing. Ph.D.
Interchangeability : N342016
Annotation -
The course is aimed at understanding of synthetic procedures enabling to control stereoselectivity of chemical reactions. It covers the basics of organic stereochemistry, analytical methods used for the study of chiral compounds and the most frequent stereoselective organic reactions.
Last update: Fialová Jana (20.12.2017)
Aim of the course -

Students will be able to:

Have a comprehensive opinion on the problem of stereoselective organic synthesis

Perform stereochemical analysis of organic compounds and design synthetic procedure for the preparation of given stereoisomers

Verify enantiomeric purity using analytical methods

Last update: Fialová Jana (20.12.2017)
Literature -

R: Eliel E. L., Wilen S. H., Doyle M. P. " Basic Organic Stereochemistry", John Wiley, 2001 (0-471-37499-7)

R: Procter G. "Stereoselectivity in Organic Synthesis", Oxford University Press, 1998 (0-19-855957-7)

R: Ward R. S. "Selectivity in Organic Synthesis" , John Wiley, 1999 (0-471-98779-4)

A: Atkinson R. S. "Stereoselective Synthesis", John Wiley, 1995 (0-471-95419-5)

Last update: Fialová Jana (20.12.2017)
Learning resources -

Lecture notes

Last update: Fialová Jana (20.12.2017)
Syllabus -

1. Types of stereoisomerism, basic stereochemical concepts, symmetry-chirality relationships, stereogenic elements, criteria for the recognition of a chiral structure

2. Stereogenic centre, central chirality simplex, non-carbon centres of chirality, enantiomers, diastereoisomers, epimers, anomers, pseudo chiral centre, relative vs. absolute configuration and its stereochemical nomenclature

3. Stereogenic axis, axial chirality, pseudochirality axis, chiral polyphenyls and other types of atropoisomerism. Planar chirality, organometallic compounds. Helicity, propelers

4. Racemic modification and its properties, resolution of racemic modifications via formation of diastereomers, chiral inclusive compounds, chromatography on chiral sorbents

5. Experimental methods for the determination of a configuration, X-ray methods. Relative configuration assignment using chemical methods, chiroptical methods and NMR methods

6. Conformation of a molecule, conformational isomers, conformational nomenclature, conformation of acyclic compounds containing polar groups and double bonds. Conformations of cyclopropane, cyclobutane, cyclopentane, pseudorotation

7. Conformations of cyclohexane, mono- and disubstituted cyclohexanes, dekalins and steroidal skeleton, cyclohexene, cyclohexadiene, cyclohexanone, conformations of middle-sized rings, trans-annular effects and reactions

8. Conformation and reactivity. Curtin-Hammet rule, reactivity of axial and equatorial substituents of cyclohexane. Homotopic, enantiotopic, and diastereotopic ligands and sides, their nomenclature, prochirality

9. Synthesis of enantiomerically pure compounds using the "chiral pool" and chirality transfer at sigmatropic rearrangements. Chiral auxiliary group, chiral agents, chiral catalysts as tools of enantioselective synthesis

10. Addition on C=O group in neighborhood of a stereogenic centre. Diastereoselectivity and enantioselectivity ïn enolate reactions, aldol reactions, and reactions of alkenyl boranes with aldehydes

11. Diastereoselectivity and enantioselectivity of electrophilic additions on C=C bond of a conjugated addition

12. Diastereoselectivity and enantioselectivity of epoxidation, Sharpless epoxidation, dihydroxylation, and amino hydroxylation

13. Diastereoselectivity and enantioselectivity of cycloaddition reactions

14. Enantioselective catalysis - formation of C-C bond

15. Double chiral induction. Chiral amplification at enantioselective catalysis. Enzymes as catalysts in enantioselective synthesis

Last update: Parkan Kamil (26.08.2020)
Registration requirements -

Organic chemistry I or Organic chemistry A and B, Strutcture and reactivity

Last update: Parkan Kamil (27.02.2018)
Course completion requirements - Czech

Napsání započtového testu, zkouškového testu a ústní zkouška.

Last update: Parkan Kamil (27.02.2018)
Teaching methods
Activity Credits Hours
Účast na přednáškách 1 28
Příprava na přednášky, semináře, laboratoře, exkurzi nebo praxi 1 28
Příprava na zkoušku a její absolvování 1 28
Účast na seminářích 1 28
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