Course

Unit 1:

Organometallic Reagents and Catalysts [14 h]Application of organometallic compounds of lithium, magnesium, boron, silicon and tin in organic synthesis. Applications of organo platinum-group metals, organonickel, organocobalt, organocopper, organozinc, organocadmium and organomercury in organic synthesis.

Unit 2:

Synthetic Strategies – I: Functional Group Interconversions[14 h]Functional group interconversions, the importance of the order of events in organic synthesis, chemoselectivity, regioselectivity, and Umpolung concept. The concept of protection and deprotection of functional groups in synthesis. Protection of amino, hydroxy, diol, carbonyl and, double and triple bonds.

Unit 3:

Synthetic Strategies II: Retro Synthesis[9 h]Disconnection Approach – synthons and synthetic equivalents, donor and acceptor synthons, disconnection, alternating polarity disconnection and steps in planning the synthesis. One and two groups C-X and C-C disconnections. Control of relative stereochemistry and enatioselectivity in carbonyl condensations. 1-5 disfunctionalised compounds.

Unit 4:

Rearrangement and Transformation Reactions[14 h]Classification of rearrangements. General mechanistic consideration, nature of migration, migratory aptitude, stereochemical aspects and memory effects in rearrangements. Rearrangement to electron deficient carbon – pinacol-pinacolone, Wagner-Meerwein, benzillic acid, Wolf, Rupe and Demjanov rearrangements. Rearrangement to electron deficient nitrogen – Hofman, Curtius, Schmidt, Lossen and Beckmann rearrangements. Rearrangement to electron deficient oxygen – Baeyer-Villiger rearrangement. Rearrangement to electron rich carbon – Fovorskii, Wittig, Neber and Stevens rearrangements. Aromatic rearrangement – Fries, Claisen and benzidine rearrangements.

Unit 5:

Asymmetric Synthesis[9 h]Principles and applications of asymmetric synthesis. Stereoselectivity in cyclic compounds, enantio-selectivity, diastereo-selectivity, enatiomeric and diastereomeric excess, stereoselective aldol reactions. Crams rule, Felkin Anh rule and Crams chelate model. Asymmetric synthesis – use of chiral auxiliaries, chiral reagents and catalysts. Asymmetric hydrogenation, epoxidation and dihydroxylation.

CO1: Design the synthesis of complex organic molecules using critical reagents

CO2: Apply photochemical organic synthesis for a greener approach

CO3: Analyse the mechanism of the light-induced organic reactions and predict the nature of the product

CO4: Scrutinize the synthesis of asymmetric organic compound

CO5: Create suitable reaction pathways to achieve specificity and selectivity in the products.

Recommended Readings

1.Warren, S., 1991. Designing organic syntheses: a programmed introduction to the synthon approach. John Wiley & Sons.

2.Li, J.J. and Corey, E.J., 2007. Name Reactions of Functional Group Transformations (Vol. 1). John Wiley & Sons.

3.Norman, R.O.C., and Coxon, J.M., 2014. Principles of organic synthesis. CRC press,

4.Gawley, R.E. and Aub, J., 2012. Principles of asymmetric synthesis. Elsevier.

5.Carey, F.A. and Sundberg, R.J., 2007. Advanced organic chemistry: part B: reaction and synthesis. Springer Science & Business Media.

6.Li, J.J., 2020. Name reactions: a collection of detailed mechanisms and synthetic applications. Springer Science & Business Media.

7.Rojas, C.M., 2015. Molecular Rearrangements in Organic Synthesis. John Wiley & Sons.