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Course module: 8RM00
8RM00
Advanced organic chemistry
Course info
Course module8RM00
Credits (ECTS)5
Category-
Course typeGraduate School
Language of instructionEnglish
Offered byEindhoven University of Technology; Biomedical Engineering; Chemical Biology;
Is part of-
Contact persondr. L.G. Milroy
Telephone3134
E-maill.milroy@tue.nl
Lecturer(s)
Co-lecturer
prof.dr. E.W. Meijer
Other course modules lecturer
Contactperson for the course
dr. L.G. Milroy
Other course modules lecturer
Responsible lecturer
dr. L.G. Milroy
Other course modules lecturer
Co-lecturer
dr. T. Noël
Other course modules lecturer
Co-lecturer
dr.ir. A.R.A. Palmans
Other course modules lecturer
Academic year2017
Period
GS3  (05/02/2018 to 22/04/2018)
Starting block
GS3
TimeslotE: E - Mo 9-10, Tu 5-8, Th 1-4
Course mode
Fulltime
Remarks-
Registration openfrom 15/11/2017 up to and including 07/01/2018
Application procedureYou apply via OSIRIS Student
Explanation-
Registration using OSIRISYes
Registration open for students from other department(s)Yes
Pre-registrationNo
Waiting listNo
Number of insufficient tests-
Number of groups of preference0
Learning objectives
The first part of the course is designed for thsoe wishing to gain experience in strategic planning for the synthesis of simple and not-so-simple organic molecules. The student will learn how an understanding of functional groups, the means to activating or protecting reactive centres, combined with retro-synthetic analysis, enables the efficient and selective construction of target molecules. Special attention will be paid to carbon-carbon disconnections. Representative syntheses from Eindhoven and the current literature will be discussed.

The second part of the course deals with the stereochemical aspects of macromolecular and organic chemistry. The molecules of life are chiral (DNA, proteins, sugars, etc) and many interactions between pharmaceutically active compounds and our body are based on chiral recognition. Hence, it is important to have insight in the meaning of chirality, the effects of chirality and how molecules can be prepared in an enantiopure manner.

The aim of this course is threefold. We start by developing the ability of students to strategically analyse known synthetic routes, followed by learning how to design a novel organic synthesis. The disconnecttion approach will play a crucial role in this part. Then, we introduce the topic of stereochemistry. Students will get more insight into which reactions occur stereoselectively and why. We will also show the importance of stereoselectivity in industry with the aid of selected examples. Finally we will discuss how amplification of chirality could have occurred and how that may have lead to the origin of homochirality (and thus of life) on earth.
Content
  1. Strategic planning for the synthesis of organic molecules
    • Recap and Introduction to The Disconnection Approach
      The Disconnection Approach
      Synthons and reagents
      Synthesis of aromatic compounds
      Important strategic elements
    • chemoselectivity
      regioselectivity
      polarity reversal
      cyclisation
      protecting groups
      C-C bond formation I
    • one group C-C disconnections:
      alcohols
      carbonyls
      C-C bond formation II
    • synthesis an utility of unsaturated C-C bonds
      alkene (Wittig-type)
      alkyne
      C-C bond formation III
    • carbonyl condensation reactions
      1,3-difunctionalised compounds
      1,5-difunctionalised compounds
      Synthesis of 5- and 6-membered rings
    • Pericyclic reactions
      Diels-Alder
      Nazarov
      Robinson Annulation revisited
      Case studies
    • Eindhoven syntheses
      examples from recent literature
  2. Synthetic approaches to enantiopure compounds
    • Definitions in stereochemistry
    • Importance of chiral compounds
      effect of chirality
      properties of stereoisomers
      chiral compounds in the pharmaceutical industry
      determination of ee
      Access to chiral compounds
    • from natural products
      asymmetric synthesis
      examples from the pharmaceutical industry
      Biotransformations/biocatalysis
    • asymmetric reductions
      aspartame process
      kinetic resolutions with lipases
      dynamic kinetic resolutions using lipases and transition metal catalysts
      Asymmetric polymerisations
    • stereoregular polyolefins
      helical polyisocyanates/polyacetylenes/polyisocyanides
      polylactides
      Synthesis of chiral compounds in continuous-flow reactors
    • homogeneous enantioselective catalysis
      organocatalysis
      Industrial enantioselective catalysis
    • Nobel prices in the field of stereochemistry (Noyori//Sharpless/Knowles)
      Chiral switch
      the story behind (S)-metolachlor, (S)-naproxen, etc.
  3. Special Topics
    • Origin of chirality in Nature
    • Amplification of chirality
Entrance requirements
You must have completed the final examination bsc program exam
Entrance requirements tests
-
Assumed previous knowledge
• 8SA00 - Introduction Organic Chemistry
• 8RB10 - Bio-organic chemistry
Previous knowledge can be gained by
-
Resources for self study
-
Required materials
Organic Synthesis: The Disconnection Approach 2nd Edition, by Stuart Warren & Paul Wyatt, Wiley, Publication Date: 21 Nov 2008 | ISBN-10: 0470712368 | ISBN-13: 978-0470712368 - Amazon voor ongeveer 30 EUR. Er is ook een werkboekje Workbook for Organi
Recommended materials
P.W. Atkins Physical Organic chemistry Chapter 12: Molecular symmetry
Anslyn & Dougherty Modern Physical Organic Chemistry Chapter 6: Stereochemistry
J. March Advanced Organic Chemistry Chapter 4: Stereochemistry
Modern Physical Organic Chemistry by E. V. Anslyn & D. A. Dougherty, University Science Books, U.S., Publication Date: 1 Jan 2005 | ISBN-10: 1891389319 | ISBN-13: 978-1891389313
Instructional modes
Assignment + exercises

General
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Remark
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Lecture

General
-

Remark
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Tests
Written examination
Test weight100
Minimum grade-
Test type-
Number of opportunities3
OpportunitiesBlock GS3, Block GS4, Block GS4
Test duration in minutes-

Assessment
-

Remark
-

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