Principles and applications of enolate alkylation: A unique strategy for construction of C-C (sp3 -sp3) bonds in asymmetric fashion

By Prof. Samik Nanda | IIT Kharagpur

Learners enrolled: 251

ABOUT THE COURSE:
Asymmetric synthesis plays a central role in the field of Organic synthesis. Chirality and biological activity is closely associated hence synthesis of small organic molecule in single enantioemric form is highly desirable. The underlying principles of asymmetric synthesis will help us enormously to design and execute suitable synthetic strategies for optically pure biologically relevant organic molecules. In this course material our main highlight will be to address the reader to become familiar with principles of enolate alkylation for the construction of new C-C bonds and its successful exploration of such strategies enroute to value added enantiopure small organic molecules.

INTENDED-AUDIENCE: UG, PG students. Relevent industrial persons

PRE-REQUISITES: Basic organic chemistry courses, Basic stereochemistry courses

INDUSTRY-SUPPORT: Pharmaceutical Industry

Summary

Course Status :	Completed
Course Type :	Elective
Duration :	8 weeks
Category :	Chemistry
Credit Points :	2
Level :	Undergraduate/Postgraduate
Start Date :	25 Jul 2022
End Date :	16 Sep 2022
Enrollment Ends :	08 Aug 2022
Exam Date :	25 Sep 2022 IST

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

Page Visits

Course layout

Week 1: Basic introductions to enolates, methods of enolate generation, structure of enolates and characterization, stereoselectivity and regioselectivity in enolate generation, transition state for enolate alkylation, different modes of asymmetric induction in enolate alkylation, intraligand and interligand asymmetric induction (intraanular/extraanular/chelate enforced intraaanular modes)
Week 2: Enolate alkylation of several carbonyl species: Seebach’s SRS (self-regeneration of stereocenter) principle and related systems, concepts and applications

Week 3: Enolate alkylation of several carbonyl species: Chiral auxiliaries in C-C bond forming reactions through enolate chemistry (Evans oxazolidinone, Camphor based N-acyloxazolidinones, Oppolzers sultam and related systems)
Week 4: Enolate alkylation of several carbonyl species: Chiral auxiliaries in C-C bond forming reactions through enolate chemistry (Myer’s ephidrene, Chiral Weinreb amide and equivalents and related systems)
Week 5:Enolate alkylation of several carbonyl species: Chiral auxiliaries in C-C bond forming reactions through enolate chemistry (Myer’s ephidrene, Chiral Weinreb amide and equivalents and related systems)
Week 6: Several methods for alkylkation of amino acids derived substrates (Schollkopf’s bis-lactim ether, William’s oxazinone, Yamada’s chiral glycine enolate and related systems)
Week 7: Aza-enolate alkylation: Ender’s RAMP/SAMP, Coltart’s cyclic carbamate hydrazone, Ellman's sulfonamide and related systems
Week 8: Organocatalytic methods for enolate alkylation (SOMO activation method), enantioselective alkylation using chiral PTC, enantioselective deprotonation of achiral systems with chiral bases, concluding remarks

Books and references

Principles of Asymmetric Synthesis: Robert E. Gawley and Jefrrey Aube; Elsevier; 2012; ISBN: 978-0-08-044860-2
Classics in Stereoselective Synthesis: E. M. Carreira and l. Kvaerno; Wiley-VCH; 2009; ISBN: 978-3-527-299966-9.
Principles and Applications of Asymmetric Synthesis: Lin, Li and A S Chan; John Wiley & Sons; ISBNs: ISBNs: 0-471-40027-0 (Hardback); 0-471-22042-6 (Electronic)

Instructor bio

Prof. Samik Nanda

IIT Kharagpur

After finishing my PhD in the field of “asymmetric synthesis with the help of enzymes” I was very much interested to carry out an independent research career in the field of asymmetric total synthesis of natural products. Since last fourteen years the research effort of my group was focused on the central theme of “asymmetric synthesis”. We have tried to explore many well developed asymmetric synthesis protocols to access our desired target molecules. We have also developed few in-house evolved asymmetric processes which was also successfully employed to access many enantiopure small organic molecules.

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: 25 September 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 6 assignments out of the total 8 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 Kharagpur. 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