NES8402 : Selectivity and Stereocontrol in Organic Synthesis
NES8402 : Selectivity and Stereocontrol in Organic Synthesis
- Offered for Year: 2024/25
- Module Leader(s): Dr Julian Knight
- Lecturer: Dr Johan Eriksson, Dr Roly Armstrong
- Owning School: Natural and Environmental Sciences
- Teaching Location: Newcastle City Campus
Semesters
Your programme is made up of credits, the total differs on programme to programme.
Semester 1 Credit Value: | 10 |
ECTS Credits: | 5.0 |
European Credit Transfer System | |
Pre-requisite
Modules you must have done previously to study this module
Pre Requisite Comment
N/A
Co-Requisite
Modules you need to take at the same time
Co Requisite Comment
N/A
Aims
To familiarise students with the key strategies for the stereocontrolled synthesis of organic compounds; to provide practise in identifying and applying such strategies; to exemplify the principles in the context of the synthesis of organic targets
Outline Of Syllabus
Stereocontrol In Organic Synthesis
Introduction to synthetic strategy, selectivity and specificity
Regioselectivity
Stereoselectivity
The aldol reaction
Asymmetric synthesis. Use of the chiral pool
Seminar covering the material on Stereocontrol
Asymmetric Catalysis
Introduction to catalysis and asymmetric catalysis. Energy diagrams. Examples of commercial asymmetric catalytic procedures.
Chiral ligands. Ligand design & the use of C2 Ligand-symmetry.
Asymmetric catalysis of reduction reactions: Rh catalysed alkene hydrogenation. Ru catalysed ketone hydrogenation. Ketone reduction via Corey oxazaborolidines.
Asymmetric catalysis of oxidation reactions: Sharpless epoxidation; Jacobsen epoxidation. Sharpless bis-hydroxylation and aminohydroxylation.
Asymmetric catalysis of carbon-carbon bond forming reactions: Cycloaddition reactions. Addition of diethylzinc to aldehydes.
Organocatalysis. Enamine chemistry. Proline catalysed aldol reactions. Mannich reactions. Aldehyde amination and oxygenation. Michael additions.
Use of enzymes as catalysts. Whole cell and isolated enzymes. Need for cofactors. Oxidoreductases.
Asymmetric catalysis on compounds which already contain stereocentres. Kinetic resolution. Dynamic kinetic resolution. Desymmetrization of meso compounds. Double stereodifferentiation. Non-linear effects. Asymmetric autoinduction, asymmetric autocatalysis, asymmetric autoamplification.
Seminars covering questions on the material on Asymmetric Catalysis
Learning Outcomes
Intended Knowledge Outcomes
• recognise and be able to comment on different synthetic strategies and methods for stereocontrol when faced
with a synthetic scheme
• understand the different classes of ‘selectivity’ and ‘specificity’
• understand and be able to use the Felkin-Anh model, chelation control, and 1,3-allylic strain to predict the
stereoselectivity of reactions
• be able to use chair transition state models to explain the stereochemical outcome of reactions when
appropriate (such as enolisations and the aldol reaction)
• understand the principles of asymmetric catalysis
• have an awareness of catalysis based on chiral metal complexes, enzymes and organocatalyst
• understand the ideas of topicity, double stereodifferentiation, and chiral amplification
• have an awareness of typical reagents and transformations used in modern organic synthesis
• be able to identify aspects of selectivity and specificity within a given synthetic scheme
• to make a reasoned choice of theoretical model
• to apply this model in order to predict or explain the observed outcome.
Intended Skill Outcomes
Subject specific or professional skills, able to:
• identify aspects of selectivity and specificity within a given synthetic scheme
Cognitive or intellectual skills, able to:
• make a reasoned choice of theoretical model
• apply this model in order to predict or explain an observed outcome.
Key skills, able to:
• plan coursework effectively
• take notes
Teaching Methods
Teaching Activities
Category | Activity | Number | Length | Student Hours | Comment |
---|---|---|---|---|---|
Structured Guided Learning | Lecture materials | 24 | 1:00 | 24:00 | PiP lectures - scheduled LTA. Pre-recorded material as a backup. |
Structured Guided Learning | Lecture materials | 1 | 1:00 | 1:00 | Online - Module introduction, module structure, assessment, reading lists and mode of delivery |
Guided Independent Study | Assessment preparation and completion | 20 | 1:00 | 20:00 | Completion of practise exercises |
Scheduled Learning And Teaching Activities | Drop-in/surgery | 1 | 1:00 | 1:00 | Week 15. (Thurs or Fri). Synchronous online support for upcoming assessment |
Scheduled Learning And Teaching Activities | Drop-in/surgery | 11 | 1:00 | 11:00 | Office hour drop in sessions |
Scheduled Learning And Teaching Activities | Drop-in/surgery | 1 | 1:00 | 1:00 | Week 15. (Thurs or Fri). Synchronous online support for upcoming assessment |
Guided Independent Study | Independent study | 1 | 42:00 | 42:00 | Background reading and revision of taught material |
Total | 100:00 |
Teaching Rationale And Relationship
The course involves the introduction of a set of principles which may be applied to the analysis and design of organic synthesis. These principles are addressed in the online lecture materials. These basic principles are consolidated in online material which exemplify these principles in the context of total synthesis of organic targets and serve to draw together the various strands of the course.
PiP delivery (3h per week) will be used to deliver the taught content and to provide feedback workshops discussing the answers to the provided online practise questions. Complete worked answers to these written problem-solving exercises are also published using a range of formats to support the learning. Short recordings of the key taught material are also provided online as an additional aid to revision.
Reading Lists
Assessment Methods
The format of resits will be determined by the Board of Examiners
Exams
Description | Length | Semester | When Set | Percentage | Comment |
---|---|---|---|---|---|
Written Examination | 120 | 1 | A | 100 | N/A |
Formative Assessments
Formative Assessment is an assessment which develops your skills in being assessed, allows for you to receive feedback, and prepares you for being assessed. However, it does not count to your final mark.
Description | Semester | When Set | Comment |
---|---|---|---|
Prob solv exercises | 1 | M | Online practise questions |
Assessment Rationale And Relationship
The alternate written assessment will consist of problem-oriented questions, some of which focus on a particular principle or set of related principles and some which require broader analysis. This is deemed an appropriate method of ascertaining the principles introduced in the course and to the extent to which they can apply these to unfamiliar situations.
The formative assessment, problem-solving exercises, with their complete worked answers are published using a range of formats to support the learning.
Study Abroad students may request to take their exam before the semester 1 exam period, in which case the format of the paper may differ from that shown in the MOF. Study Abroad students should contact the school to discuss this.
Timetable
- Timetable Website: www.ncl.ac.uk/timetable/
- NES8402's Timetable
Past Exam Papers
- Exam Papers Online : www.ncl.ac.uk/exam.papers/
- NES8402's past Exam Papers
General Notes
Original Handbook text:
Welcome to Newcastle University Module Catalogue
This is where you will be able to find all key information about modules on your programme of study. It will help you make an informed decision on the options available to you within your programme.
You may have some queries about the modules available to you. Your school office will be able to signpost you to someone who will support you with any queries.
Disclaimer
The information contained within the Module Catalogue relates to the 2024 academic year.
In accordance with University Terms and Conditions, the University makes all reasonable efforts to deliver the modules as described.
Modules may be amended on an annual basis to take account of changing staff expertise, developments in the discipline, the requirements of external bodies and partners, and student feedback. Module information for the 2025/26 entry will be published here in early-April 2025. Queries about information in the Module Catalogue should in the first instance be addressed to your School Office.