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Module

CHY8420 : Selectivity and Stereocontrol in Organic Synthesis

  • Offered for Year: 2021/22
  • Module Leader(s): Dr Julian Knight
  • Lecturer: Dr Johan Eriksson
  • Owning School: Natural and Environmental Sciences
  • Teaching Location: Newcastle City Campus
Semesters
Semester 1 Credit Value: 10
ECTS Credits: 5.0

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. Temperature dependence of asymmetric induction. Examples of commercial asymmetric catalytic procedures.
Chiral ligands. Ligand design. Ligand-symmetry. Energy diagrams for C1- and C2-symmetric processes.
Metals used in asymmetric catalysis. Role of the metal. What makes a good asymmetric catalyst?
Asymmetric catalysis of reduction reactions. Alkene hydrogenation. Ketone reduction.
Corey oxazaborolidines. Asymmetric catalysis of oxidation reactions. Sharpless epoxidation. Jacobsen epoxidation and related reactions.
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

Teaching Methods

Teaching Activities
Category Activity Number Length Student Hours Comment
Structured Guided LearningLecture materials11:001:00Online - Module introduction, module structure, assessment, reading lists and mode of delivery
Structured Guided LearningLecture materials241:0024:00PiP lectures - scheduled LTA. Pre-recorded material as a backup.
Guided Independent StudyAssessment preparation and completion201:0020:00Revision of taught material
Scheduled Learning And Teaching ActivitiesDrop-in/surgery111:0011:00Office hour drop in sessions
Scheduled Learning And Teaching ActivitiesDrop-in/surgery11:001:00Week 15. (Thurs or Fri). Synchronous online support for upcoming assessment
Scheduled Learning And Teaching ActivitiesDrop-in/surgery11:001:00Week 15. (Thurs or Fri). Synchronous online support for upcoming assessment
Guided Independent StudyIndependent study114:0014:00Completion of summative alternative assessment
Guided Independent StudyIndependent study128:0028:00Revision of taught material
Total100:00
Jointly Taught With
Code Title
CHY8834Selectivity and Stereocontrol in Organic Synthesis
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.

Online via Canvas - A combination of short recordings of lecture material and text published on VLE. Exercises (e.g. written problem-solving exercises) together with complete worked answers will be published using a range of formats to support the learning. Lecture content will be delivered by week with the equivalent of 3 lectures per week for 8 weeks of teaching.

Assessment Methods

The format of resits will be determined by the Board of Examiners

Exams
Description Length Semester When Set Percentage Comment
Written Examination1201A100N/A
Exam Pairings
Module Code Module Title Semester Comment
CHY8834Selectivity and Stereocontrol in Organic Synthesis1N/A
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.

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.

Reading Lists

Timetable