Advanced Organic Chemistry 1200-2EN-AOCHLE1M
The lecture is aimed at presentation of basic concepts and modern methods of asymmetric organic synthesis.
The first part of the lecture will introduce fundamental concepts and definitions: chemoselectivity, regioselectivity, stereoselectivity, enantio- and diastereoselectivity. Next, methods for determination of enantiomeric and diastereoisomeric excess will be critically discussed. The next lectures will focus on additions of organometalic reagents to carbonyl group including thorough discussion of Cram and Felkin-Ankh models, with emphasis on broad applicability of Felkin-Ankh model in asymmetric synthesis. Following lectures will introduce methods for synthesis of chiral molecules with new stereogenic centers based on EPC synthesis, chiral auxiliary and chiral catalyst. The emphasis will be put on the modern enantioselective synthesis. Each concept will be thoroughly illustrated with chemical literature examples of important organic reactions:
- basics of homo- and hetero-Diels-Alder reactions,
- organometallic additions to carbonyl group, including Grignard reagents, organolithium compounds, dialkylzinc compounds,
- asymmetric allylic alkylation catalyzed by palladium, molybdenum and iridium complexes.
- basics of organocatalysis
Lecture = 30 hours.
Individual preparation for each lecture (1.0 h weekly) = 15 hours.
Preparation for the exam = 25 hours.
Together = approximately 70 hours.
Type of course
Mode
Prerequisites (description)
Learning outcomes
After completing the lecture, a student:
a) should be able to choose best method for determination of enantioselectivity
b) should be able to build a stereochemical model for simple enantio- and diastereoselective reactions
c) have a basic knowledge about most important methods for the stereogenic center generation.
Assessment criteria
Stationary final examination with open-ended questions. Writing time 90 minutes.
Practical placement
Not applicable
Bibliography
References to appropriate articles in chemical journals will be given during the course.
Additional information
Additional information (registration calendar, class conductors, localization and schedules of classes), might be available in the USOSweb system: