Syllabus: Course Dates
Week 1: Course introduction
Retrosynthetic analysis: Strategic disconnections
Retrosynthetic analysis: Disconnections with polarity reversal (umpolung)
Week 2 and 3: Oxidations
I. Metal Based Reagents
1. Chromium Reagents
2. Manganese Reagents.
3. Silver
4. Ruthenium
5. Other metals
II Non-Metal Based Reagents
1. Activated DMSO
2. Peroxides and Peracids
3. Oxygen/ ozone
4. Others
III. Epoxidations
Week 4: Reduction (Reduction of Carbonyl and Other Functional Groups)
i. Hydride-Transfer Reagents
ii. Hydrogen-Atom Donor
iii. Dissolving Metal Reductions
Week 5: First Midterm Exam
Week 6: Carbon- Carbon Bond Formation
i) Alkylation of enolates, enamines and hydrazones
ii) Alkylation of heteroatom stabilized anions
iii) Umpolung Smith
iv) Organometallic Reagents
v) Sigmatropic Rearrangements
vi)
Week 7: Functional Group Interconversions
i. sulfonates
ii. halides
iii. nitriles
iv. azides
v. amines
iv. esters and lactones
iiv. amides and lactams
Week 8 and 9: Methods in Organic Synthesis - Retrosynthetic Analysis
i. Retrosynthesis.
Importance of synthesis. Concepts & terminology of retrosynthetic analysis.
Problem of identifying disconnections. Guidelines for choosing disconnections & evaluating routes.
ii. Functional Group Interconversions
Example problem illustrating concepts for FGI. Chemoregio- and stereoselectivity issues.
iii. Retrosynthesis of Hydrocarbon Targets.
Preparation of alkenes. Revision of Wittig and Julia coupling reactions. Prep from alkynes. Forming C–C bonds by cross coupling reactions. Formation of organometal reagents.
iv. Example problem illustrating C–C, C=C formation.
Scope of SN2 reaction using carbon nucleophiles.
v. Retrosynthesis of Monofunctional Targets.
Revision of key reactions: nucleophilic addition to carbonyl & carboxyl compounds, enolate reactions, conjugate additions.
vi. Example problem illustrating addition to carbonyls and enolate reactions. Disconnect
at branch points, chains from rings.
vii. Problem solving/tutorial.
viii. Example problem illustrating conjugate addition and tandem conjugate
addition/enolate alkylation.
Ix Retrosynthesis of Difunctional Targets. Disconnect between functional groups. Rogletimide: natural polarity.
x. Reversed polarity synthons Epoxides, cyanide, dithianes, etc.
Example problem
Week 10: Second Midterm Exam
Week 11 : Development of the metathesis method in organic synthesis
i. Introduction.
ii. The discovery of the olefin metathesis reaction.
iii. Unravelling how metathesis works - the Chauvin mechanism
iv. Schrock`s creation of the first well-defined useful catalysts
v. Grubbs discovery of practical catalysts
vi. The multitude of applications
vii. Further catalyst development
viii. Consequences and application
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