3 ECTS credits
80 h study time
Offer 1 with catalog number 4023194ENR for all students in the 1st semester at a (E) Master - advanced level.
Theory (“HOC”):
This course deals with advanced topics within the field of asymmetric synthesis with special emphasis on modern catalytic enantioselective methods. The following topics are discussed:
1) General principles: stereochemical vocabulary, analytical methods and general concepts in asymmetric synthesis.
2) Asymmetric addition to carbonyl compounds (chiral auxiliaries, catalytic methods and autocatalysis)
3) The use of chiral enolates and organocatalysis. Enolate alkylation and asymmetric aldol reactions (Zimmerman-Traxler transition state, etc.)
4) Asymmetric additions to C=C bonds
5) Asymmetric reductions and oxidations
Practical laboratory exercise (“WPO”)
In the laboratory exercise the students will carry out a catalytic, enantioselective transformation such as a catalyzed addition of diethyl zinc to an aldehyde or an organocatalytic Diels-Alder reaction catalyzed by MacMillan’s catalyst. This is followed by determination of the enantiomeric ratio using an appropriate method such as gas chromatography on a chiral phase. The experiment will be documented in a written report including analysis of the stereoselectivity.
Course material:
- (recommended) “Organic Chemistry”, Clayden , Greeves & Warren, Oxford Univ. Press; 2nd Edition 2012
- “March's Advanced Organic Chemistry”, Michael B. Smith, Wiley, 7th Ed. 2013
- “Advanced Organic Chemistry”, Carey and Sundberg, Springer, 5th Ed. 2007
- “Classics in Stereoselective Synthesis”, Erick M. Carreira and Lisbet Kvaerno, Wiley, 1st Edition, 2009
- “Asymmetric Synthesis: The Essentials“ Mathias Christmann and Stefan Bräse, 2nd Edition, Wiley, 2007
Additional course material will be available on the learning platform (powerpoint slides).
The student has good knowlegde of the methods and principles of asymmetric synthesis including insight in the reaction mechanisms in the field of asymmetric synthesis. The student is able to design and execute the synthesis of chiral molecules and has the ability to understand and follow the scientific literature in the field of asymmetric synthesis.
The final grade is composed based on the following categories:
Other Exam determines 100% of the final mark.
Within the Other Exam category, the following assignments need to be completed:
The assessment consists of the following categories of assignments:
oral examination preceded by a written preparation (30 min preparation followed by 30 min oral examination)
written report about the laboratory exercises
(All categories need to be fulfilled in order to be eligible for obtaining a final grade)
Oral exam determines 85% of the final grade
Written report 15% of the final grade (evaluated at the oral exam)
This offer is part of the following study plans:
Master of Bioengineering Sciences: Cell and Gene Biotechnology: Medical Biotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Cell and Gene Biotechnology: Molecular Biotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Cell and Gene Biotechnology: Agrobiotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Chemistry and Bioprocess Technology: Food Biotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Chemistry and Bioprocess Technology: Chemical Biotechnology (only offered in Dutch)
Master of Bioengineering Sciences: Chemistry and Bioprocess Technology: Biochemical Biotechnology (only offered in Dutch)
Master of Chemistry: Analytical and Environmental Chemistry
Master of Chemistry: Chemical Theory, (Bio)Molecular Design and Synthesis