NYU CHEM-UA 911: Advanced Organic Chemistry Tuesday and Thursday, 3:30-4:45 PM, GCASL, Room 461 and on Zoom

Instructor: Dirk Trauner Office: 100 Washington Square East, Room 712 Phone: (212) 998-3747 Email: [email protected] Office Hours: Thursdays 1 PM-2 PM, on Zoom.

Teaching Assistant: Collin Hunter Witt Email: [email protected] Recitation: Wednesdays 8:00 AM-9:15 AM in KIMM 606

Overview This course focuses on stereochemistry, stereoselective reactions, and their strategic application in the synthesis of complex molecules. Topics include symmetry and chirality, oxidations and reductions, aldol additions, pericyclic reactions and other reactions that proceed through cyclic transitions states, olefinations, transition metal catalyzed reactions, and protecting group strategies. The material will be illustrated by numerous total syntheses of natural products and of drugs, many of which are drawn from the instructor’s research. Based on this course, students should be able to read the modern literature, develop independent research proposals in organic chemistry, and make judicious choices for graduate school.

Handouts, Molecular Models and Molecular Modeling , Online Resources An extensive set of handouts will be issued on a weekly basis through NYU Classes. There will be no required textbook although the Clayden-Reeves-Warren book is recommended for further reading: https://global.oup.com/academic/product/organic-chemistry-9780199270293?cc=us&lang=en& We also recommend that you obtain a molecular software, such Avogadro or Pymol. Avogadro is a that is free of charge: http://avogadro.cc. Pymol is free for college students, following online registration: https://pymol.org. Alternatively, you can purchase an NYU student edition of Spartan, a much more elaborate program that not only allows you to look at structures but also to perform simple as well as highly sophisticated calculations. In addition, we will provide a brief introduction to Reaxys database, which is available through the NYU library network: https://www.reaxys.com/#/search/quick

Problem Sets: We will issue weekly problem sets, 12 in total.

Exams: There will be two “midterm” exams plus a final exam.

Exam Dates: 1st Exam Thursday, October 15, 2020 2nd Exam Thursday, November 12, 2020 3rd and Final Exam Tuesday, December 15, 2020

Final Grade: The final grade will be calculated based on the following percentages: Class participation, incl. problem sets (10%). First Exam (20%), Second Exam (30%), Final Exam (40%; cumulative).

Course Schedule (tentative, subject to change) 1) 09/03/30 Introduction, Goals and Philosophy, Review 2) 09/08/19 Stereochemistry I: Symmetry and Chirality 3) 09/10/20 Stereochemistry II: Molecular Point Groups 4) 09/15/20 Principles of Stereoselective Reactions 5) 09/17/20 Oxidations and Reductions of Carbonyl Compounds 6) 09/22/20 Oxidations and Reductions of Alkenes

7) 09/24/20 Hydroboration and Hydroboration-Oxidation 8) 09/29/20 Aldol Additions I: Simple Diastereoselection 9) 10/01/20 Aldol Additions I: Induced and Double Diastereoselection 10) 10/06/20 Asymmetric Aldol Additions 11) 10/08/20 Cross-Coupling Reactions I 12) 10/13/20 Cross-Coupling Reactions II and other TM-catalyzed reactions 13) 10/15/20 1st Exam 14) 10/20/20 Olefinations I 15) 10/22/20 Olefinations II 16) 10/27/20 Allyl Additions 17) 10/29/20 Diels-Alder Reactions I 18) 11/03/20 Diels-Alder Reactions II 19) 11/05/20 1,3-Dipolar Cycloadditions I 20) 11/10/20 1,3-Dipolar Cycloadditions II 21) 11/12/20 2nd Exam 22) 11/17/20 Electrocyclizations 23) 11/19/20 Sigmatropic Rearrangements 24) 11/24/20 Olefin Metathesis I 25) 12/01/20 Olefin Metathesis II 26) 12/03/20 Radical Reactions I 27) 12/08/20 Radical Reactions II: Photoredox Reactions 28) 12/10/20 Enamines Imines and Mannich Reactions 29) 12/15/20 3rd and Final Exam