Essentials of Oxidation, Reduction and C-C Bond Formation. Application in Organic Synthesis

By Prof. Yashwant D Vankar | IIT Bombay and IISER Thiruvananthapuram

Learners enrolled: 665

In this course I will deal, in detail, of some of the modern and important methods/aspects of
(a) Oxidation
(b) Reduction and
(c) C-C Bond Formation
with special emphasis on addressing
(i) Selectivity [Regio-, Chemo- and Stereo- (Enantio- and Diastereoselectivity)]
(ii) Mechanism
(iii) Stereochemistry (wherever necessary) and
(iv) Application in solving some synthetic problems using the synthetic reactions discussed
Note: (1) I will give appropriate references of books, research papers, and reviews for people for extra information as and when they need. (2) It is expected that this course will help MSc students appearing for NET, GATE and GRE/AGRE examinations. It will also help chemists working in industry who use such reactions in their daily work.

INTENDED AUDIENCE : MSc in Chemistry

PREREQUISITES : BSc (Chemistry: specially organic chemistry courses)

INDUSTRIES SUPPORT : Dr. Reddy’s Laboratory, Syngene, Bristol-Myers Bangalore, Syngenta (Goa), Pharma Industries

Summary

Course Status :	Completed
Course Type :	Core
Language for course content :	English
Duration :	12 weeks
Category :	Chemistry
Credit Points :	3
Level :	Postgraduate
Start Date :	24 Jan 2022
End Date :	15 Apr 2022
Enrollment Ends :	07 Feb 2022
Exam Date :	24 Apr 2022 IST

Note: This exam date is subject to change based on seat availability. You can check final exam date on your hall ticket.

Page Visits

Course layout

Week 1:Lecture 1: Introduction to organic synthesis, importance of selectivity and basics of oxidation of alcohols and development of sulfur based oxidations: Swern oxidation and related concepts
Lecture 2: Continuation of Swern oxidation and the utility of intermediates derived from Swern oxidation including Pummerer intermediates Lecture 3. Oxidations using selenium compounds such as SeO2 and organoselenium compounds

Week 2:Lectures 4 and 5: Dess-Martin, IBX and related hypervalent iodine based oxidations
Lecture 6: Silver carbonate/celite, Prevost reactions and its modern variation. Microbial oxidations such as Pseudomonas Putida etc.

Week 3: Lecture 7: Oxidations with RuO4 and other Transition metal catalysed oxidations
Lecture 8: Tamao-Fleming Oxidation
Lecture 9: Oxidations with Dimethyl dioxirane (DMDO) and 2-sulfonyloxaziridines and chiral versions
Lecture 10:Oxidations at unfunctionalised carbons, Photosensitized oxidations

Week 4: Lectures 11-14: Reduction of Carbonyl compounds with Boron and Aluminium based reagents such as Luche Reduction, NaCN(BH3), DIBAL, Red-Al, L-and K-Selectrides, Superhydrides and associated selectivities.

Week 5: Lecture 15: Low Valent Titanium species and Microbial reductions (NADH model etc.)
Lecture 16: Dissolving Metal Reductions
Lecture 17: Reduction with Silanes

Week 6: Lectures 18 and 19: Sharpless epoxidation and synthetic utility of the chiral epoxy alcohols
Lecture 20: Katsuki-Jacobsen epoxidation and mechanistic details
Lectures 21 : OsO4 based and related Sharpless Asymmetric Dihydroxylation

Week 7: Lecture 22: Corey’s oxazaborilidines in asymmetric reductions
Lecture 23: Noyori’s Ruthenium catalysed reduction of ketones
Lecture 24: Asymmetric Hydrogenations with BINAP

Week 8: Lecture 25: C-C Bond formation via Carbanions alpha to electron withdrawing groups
Lecture 26: Boron and Silicon Enolates: Formation and Use in C-C Bond Formation
Lecture 27: Imines in C-C Bond Formation
Lecture 28: Simmons-Smith Cyclopropanation in Organic Synthesis

Week 9: Lectures 29-32: Use of Allyl Boron, Allyl and Vinyl Silanes and Allyl Tin compounds in C-C Bond Formation

Week 10: Lecture 33: Introduction to SAMP and RAMP chiral ligands for asymmetric C-C bond formation
Lecture 34: Introduction to Oppolzer’s Sultam based chiral ligands and their reactions for organic synthesis
Lectures 35 and 36: Evans’ Oxazolidinone for asymmetric synthesis

Week 11: Lectures 37 and 38: Synthesis of selected natural products using above discussed methods of oxidation, reduction and C-C Bond formations

Week 12:Lectures 39 and 40: Synthesis of selected natural products using above discussed methods of oxidation, reduction and C-C Bond formations

Books and references

(1) Organic Synthesis by M.B. Smith

(2) Modern Synthetic Methods by W Carruthers

(3) Classics in Total Synthesis (Parts I-III) by K. C. Nicolaou

(4) Organic Mechanisms by R. Bruckner

(5) The Way of Synthesis by T. Hudlicky and J. W. Redd

(6) A Few Reviews/Papers Published in Standard Journals

Instructor bio

Prof. Yashwant D Vankar

IIT Bombay and IISER Thiruvananthapuram

1. I am an Emeritus Professor at the School of Chemistry, Indian Institute of Science Education and Research, Thiruvananthapuram (IISER, Thiruvananthapuram) since November 2019. Prior to that I was a Professor of Chemistry at IIT Kanpur since March 1981 to October 2018. 2. Over the years (more than 37 years at IIT Kanpur) I have taught a variety of compulsory and elective courses to Ph. D., M.Sc, and B.Tech students which were well appreciated by the student community. Now, at present also I am teaching organic chemistry at IISER Thiruvananthapuram. 3. Besides getting a number of commendation letters, almost every semester, from the Director of IIT Kanpur for excellent teaching, I was given Distinguished Teachers Award by IIT Kanpur in 2015. 4. I have also been very active in research in organic chemistry. 5. I have guided 41 PhDs, more than 60 MSc research projects, and a few post-doctoral fellows. I have published close to 180 papers in various important international journals. 6. A number of research projects were also funded to me from various funding agencies such as DST, CSIR, MHRD etc. 7. With this rich experience and background, I wish to put in efforts for the benefit of other students/chemists through NPTEL courses.

Course certificate

The course is free to enroll and learn from. But if you want a certificate, you have to register and write the proctored exam conducted by us in person at any of the designated exam centres.
The exam is optional for a fee of Rs 1000/- (Rupees one thousand only).
Date and Time of Exams: 24 April 2022 Morning session 9am to 12 noon; Afternoon Session 2pm to 5pm.
Registration url: Announcements will be made when the registration form is open for registrations.
The online registration form has to be filled and the certification exam fee needs to be paid. More details will be made available when the exam registration form is published. If there are any changes, it will be mentioned then.
Please check the form for more details on the cities where the exams will be held, the conditions you agree to when you fill the form etc.

CRITERIA TO GET A CERTIFICATE

Average assignment score = 25% of average of best 8 assignments out of the total 12 assignments given in the course.
Exam score = 75% of the proctored certification exam score out of 100

Final score = Average assignment score + Exam score

YOU WILL BE ELIGIBLE FOR A CERTIFICATE ONLY IF AVERAGE ASSIGNMENT SCORE >=10/25 AND EXAM SCORE >= 30/75. If one of the 2 criteria is not met, you will not get the certificate even if the Final score >= 40/100.

Certificate will have your name, photograph and the score in the final exam with the breakup.It will have the logos of NPTEL and IIT Bombay.It will be e-verifiable at nptel.ac.in/noc.

Only the e-certificate will be made available. Hard copies will not be dispatched.

Once again, thanks for your interest in our online courses and certification. Happy learning.

- NPTEL team

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