COURSE OUTLINE                                                                                                             FALL 2020

 

Course Title:    Advance Stereochemistry

Course Code: CHEM-7139

Credit Hours:  3

Instructor:       Dr Abdul Rauf Raza, Associate Professor

Email:              [email protected]

 

DESCRIPTION & OBJECTIVES

 

Stereochemistry is the study of the relative arrangement of atoms or groups in a molecule in 3D space. Stereochemistry of molecules dictates isomerism, chemical and biochemical reactivity. These days chiral drugs have become an integral part of pharmaceutical industry and replacing racemic (enantio impure) drugs. A basic concept on 3D structures, conformations of molecules, asymmetric synthesis, other stereochemical principles and attributes are essential.

This course is aimed at our BS/MSc course CHEM-372 / 561 (Organic Chemistry-I) course as foundation knowledge. This course (CHEM-740, Advance Stereochemistry) shall lay foundation for asymmetric transformations with an emphasis on mechanisms, structure-reactivity relationships and applications in organic synthesis.

 

READINGS

 

  1. Eliel, E. L. Wilen S. H. and Mander, L. N. Stereochemistry of Organic Compounds. John Wiley & Sons, New York (1994).
  2. Morris, D. G. Stereochemistry. RSC (Cambridge), UK (2001).
  3. North, M. Principles and Applications of Stereochemistry. Stanley Thornes Publishers Ltd (Cheltenham), UK (1998).
  4. Nasipuri, D. Stereochemistry of Organic Compounds: Principles and Applications. New Age International Ltd, New Delhi (2012).
  5. Gal, J., Stereochemical Vocabulary for Structures …. Chirality, 23 (2011), 647-659 (A review article).

 

CONTENTS

 

Stereochemistry of cyclic and fused systems; stereochemical outcome of addition, substitution, elimination, pericyclic reactions and molecular rearrangements; Felkin-Anh’s Principle; ee and de; stereoselectivity vs stereospecificity; asymmetric syntheses involving the use of chiral pool, chiral reagents and chiral catalysts, resolution methods.

                                                                                                                           

COURSE SCHEDULE

Week

Topics and Readings

Dates

1

Polarimetry, elements of symmetry (Cn, σv, σh, Sn)

November 2, 2020

Elements of chirality, classification of isomers

November 3, 2020

2

Projection of 3D models (molecules) to 2D

November 9, 2020

Configuration vs conformation; relative & absolute configuration

November 10, 2020

3

Topicity of ligands, faces & surfaces

November 16 & 17, 2020

4

Cyclic & fused (decalene etc.) ring systems

November 23 & 24, 2020

5

Configuration, configurational isomers with asymmetric centre(s) (enantiomers, diastereomers, epimers etc.)

November 30, 2020

December 1, 2020

6

Configurational isomers with axis of chirality like atropisomers (biphenyls, terphenyls, allens, spiranes etc.) and plane of chirality

December 7, 2020

December 8, 2020

7

Stereoselectivity vs. stereospecificity

December 14, 2020

Stereochemical outcome of addition (C=C, C≡C, C=X where X = O, S, NR) reactions

December 15, 2020

8

Mid-Term Examination (December 28 2020 to January 1, 2021)

9

Stereochemical outcome of elimination reactions

January 4 & 5, 2021

10

Stereochemical outcome of substitution reactions

January 11, 2021

January 12, 2021

12

Stereochemical outcome of pericyclic reactions & molecular rearrangements

January 18, 2021

January 19, 2021

13

Asymmetric synthesis including chiral pool approach

January 25, 2021

January 26, 2021

14

Asymmetric synthesis involving chiral substrates and chiral reagents

February 1, 2021

February 2, 2021

15

Asymmetric catalysis

February 8, 2021

February 9, 2021

16

Felkin Anh’s Model

February 15 & 16, 2021

17

Resolution of Racemic modifications

February 22 & 23, 2021

18

Final Examination (March 1-5, 2021)

 

 

Note: You can reserve one week for sessional or mid-term exam, and, if you wish, one week for student presentations of the assigned research project

 

RESEARCH PROJECT

 

Presentation on different current topics in due course after mid term examination on Fridays as per time table.

 

ASSESSMENT CRITERIA

 

Mid Term Examination:          30% (100% objective type)

Sessional:                                20% (Attendance = 10%, Assignments = 5%, Presentation / conduct = 5%)

Presentation:                           5% (included in sessional marks)

Participation:                           5% (included in sessional marks)   

Final examination:                   50% (60% subjective type; 40% objective; premid :postmid course = 3:7)

 

RULES AND REGULATIONS

 

Minimum attendance required for sitting in Mid/Final Exam. = 75%

 

Course Material