Stereoselective Syntheses - N342016
Title: Stereoselektivní syntézy
Guaranteed by: Department of Chemistry of Natural Compounds (342)
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: 15 / 15 (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
Level:  
For type:  
Note: course can be enrolled in outside the study plan
enabled for web enrollment
Guarantor: Parkan Kamil Ing. Ph.D.
Examination dates   
Annotation -
Last update: TAJ342 (30.09.2013)
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.
Aim of the course -
Last update: TAJ342 (30.09.2013)

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

Literature -
Last update: TAJ342 (30.09.2013)

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)

Learning resources -
Last update: TAJ342 (30.09.2013)

Lecture notes

Syllabus -
Last update: TAJ342 (30.09.2013)

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

2. Stereogenic center, central chirality simplex, non-carbon centers of chirality, enantiomers, diastereoisomers, epimers, anomers, pseudo chiral center, 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 center. 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. Double chiral induction. Chiral amplification at enantioselective catalysis. Enzymes as catalysts in enantioselective synthesis

Registration requirements -
Last update: TAJ342 (30.09.2013)

Organic chemistry I

Strutcture and reactivity

Teaching methods
Activity Credits Hours
Obhajoba individuálního projektu 0,5 14
Účast na přednáškách 1 28
Příprava na přednášky, semináře, laboratoře, exkurzi nebo praxi 0,5 14
Práce na individuálním projektu 0,5 14
Příprava na zkoušku a její absolvování 1 28
Účast na seminářích 0,5 14
4 / 4 112 / 112
Coursework assessment
Form Significance
Regular attendance 20
Defense of an individual project 10
Examination test 25
Continuous assessment of study performance and course -credit tests 20
Oral examination 25