Catalysis in Organic Reactions

Numbering Code G-ENG13 7H213 LJ60 Year/Term 2021 ・ First semester
Number of Credits 1.5 Course Type Lecture
Target Year Target Student
Language Japanese Day/Period Wed.1
Instructor name OOE KOUICHI (Graduate School of Engineering Professor)
Outline and Purpose of the Course Students will learn the basics of homogeneous catalytic reactions as key reactions used in total synthesis research of natural products, and deepen their understanding of efficient construction methods of carbon skeletons. We will also discuss organic synthesis reactions and various reactants that are highly useful from the viewpoint of functional group selectivity and stereoselectivity. At the end of each lecture, a quiz (confirmation test) on what you learned in the unit will be conducted to cultivate the ability to apply homogeneous catalytic reactions and organic conversion methods.
Course Goals ・ Construction of retrosynthetic routes for structurally complex compounds
・ Chemistry of protecting groups
・ Basic organometallic reactions
・ Cross-coupling reaction
・ Asymmetric synthesis
・ How to use synthetic chemistry of alkene complexes
・ How to use synthetic chemistry of metathesis reactions
・ Asymmetric aldol reaction
・ Organic catalysts
・ Diels-Alder reaction
・ Cyclization oligomerization reaction of alkynes
・ How to use synthetic chemistry of carbene and nitrene complexes
Schedule and Contents Total synthesis of Minfiensine (2 sessions)
・ Guidance on general lectures
・ Transmetallation reaction
・ Suzuki / Miyaura coupling reaction
・ Asymmetric Mizoroki-Heck reaction
・ Synthetic chemical utilization of alkene complexes

Total synthesis of Vitamin E (1 session)
・ Asymmetric Domino Wacker-Heck reaction

(+)-Total synthesis of Laurenyne (1 session)
・ CBS asymmetric reduction reaction
・ [3,3] Sigmatropic reaction

(+)-Total synthesis of Cyanthiwigin U (2 sessions)
・ Alkene metathesis reaction
・ Chiral pool method

Total synthesis of Miriaporone 4 (2 sessions)
・ Evans aldol reaction
・ Alcohol oxidation reaction by TEMPO and IBX
・ 1, 3-Dipole addition reaction

Total synthesis of BIRT-377 (1 session)
・ Organic catalyst
・ Pinnick oxidation reaction
(-)-Total synthesis of Tetrodotoxin (2 sessions)
・ Reaction of carbene complex
・ Reaction of nitrene complex
・ Chiral pool method
・ Felkin-Anh model
Evaluation Methods and Policy A quiz is given at the end of each lecture, and results of the quiz and final exam for each lecture are evaluated comprehensively.
Course Requirements Lectures on synthetic organic chemistry and organometallic chemistry will proceed on the premise that you have already acquired basic knowledge at the undergraduate level.
Study outside of Class (preparation and review) Students should briefly glance over handouts and References to prepare for the contents of each unit before attending any lecture. In addition, students will actively work on assignments given in each teaching session to deepen their understanding of these contents. It is advisable for students to devote twice the amount of time spent in teaching sessions to preparing for and reviewing the teaching sessions.
Textbooks Textbooks/References Distribute materials to be used with the content of the lecture.
References, etc. Translated by Shinji Murai, "Organic Synthesis by Hegedas Transition Metals" (2011, Tokyo Kagaku Dojin), Translated by Takanori Shibata, et al., "Synthetic Organic Chemistry" by RK Parashar (2011, Tokyo Kagaku Dojin), W. Carruthers and I. Coldham "Modern" Methods of Organic Synthesis 4th Ed .; Cambridge University Press: Cambridge, 2004. (Cambridge, 2004.), J. F. Hartwig "Organotransition Metal Chemistry" (University Science Books) ISBN: 978-1-891389-53-5