Stereochemie und Stereoselektive Synthese

VL 21222

Termine

ab 14.04.2015, Di, 10-12, 14-15 HS Kristallographie.
Oral exams, approx. 30 min., Monday 20.7.15, Tuesday 21.7.15 and Wednesday 22.7.15
exam dates
the exams will take place in room 36.07, Takustr. 3.
the lecture will be taught in English

Registration

Please, register for the course in Campus Management as usual. You will need to sign up separately for the oral exam in lecture on July 7th.

Bitte melden Sie sich im Campus Management für das Modul an. Wenn Sie sich aus irgendeinem Grund nicht im Campus Management anmelden könne (z.B. weil Sie noch im Bachelor oder nach der "alten" Masterordnung studieren), dann wenden Sie sich bitte mit einer kurzen E-mail an Christiane Müller vom Studienbüro.
Für die mündlichen Prüfungen melden Sie sich nochmal gesondert bei mir in der Vorlesung am 7. Juli an.

Topics

1. Symmetry Elements, Symmetry Operations, Point Groups
2. Classification of Stereoisomers and Groupings
3. Local Chirality, Stereogenicity, Chirotopicity
4. Systematic Notation of Stereoisomers
5. Stereoselectivity
6. Conformational Analysis
7. Enolates and their Alkylation
8. Aldol reactions
9. Allylation, Crotylation of Aldehydes
10. Allylic Alkylation
11. Epoxidation, Kinetic Resolution
12. Dihydroxylation
13. Hydrogenation of Carbonyl Groups
14. Hydrogenation of Olefins
15. Diels–Alder reactions
16. Baldwin's Rules
17. Thorpe-Ingold-Effect

Hand-Outs and Links

Introduction to Stereochemistry
Problems 1

CIP sequence rules: Angew. Chem. 1966, 78, 413; Angew. Chem. 1982, 96, 614

IUPAC recommendations for drawings: general, stereo
IUPAC recommendations for stereochemical terminology.

Stereoselectivity
Conformational Analysis
Enolate Generation and Alkylation
Aldol Reactions

The Felkin-Anh-Eisenstein model for addition of nucleophiles to carbonyl groups. Original publication

Problems 5
Aldol Reactions, continued
Allylation and Crotylation of Aldehydes
Problems 6 with solution
Kinetic Resolution, Epoxidation, Dihydroxylation. There was a mistake on page 97, corrected version
Problems 7
Hydrogenation of Olefins and Ketones
Problems 8, Chem. Eur. J. 2014, 20, 17360
Asymmetric Allylic Alkylation
Problems 9, Chem. Sci. 2013, 4, 709
Baldwin's Rules
Thorpe Ingold Effect
Problems 10, Angew. Chem. Int. Ed. 2015, 54, 1929
Aggerwal's Lithiation-Borylation Methodology