Chem 745

CHEM 745 – Organic Synthesis

This course is designed to cover the fascinating art of organic synthesis. We will go in-depth to cover the principle reactions leading to carbon-carbon bond formation and functional group transformations. We will discuss the strategies and methods for organic synthesis. We will cover the reactivity, methodology, and mechanisms of the reactions of alkenes and alkynes, oxidations and reductions, carbon nucleophiles, pericyclic reactions and metal-mediated reactions. Aspects of selectivity are paramount for these topics.

Syllabus (pdf)

Notes and Handouts

Introduction Presentation (pdf)
Stereochemistry Terms (pdf)
Olefination part 1 (pdf)
Olefination part 2 (pdf)
Asymmetric Alkylation (pdf)
Aldol Stereoselectivity (pdf)
Proline Catalysis (pdf)
Oxidation Examples (pdf)
Asymmetric Aminohydroxylation
Hydrogenation Examples
Oxygen and Nitrogen protecting groups
Baldwin’s Rules – CHEM REV article on alkyne cyclization revisions to Baldwin’s Rules

Review – Cyclopropane Natural Products
Review – Stereoselective Cyclopropanations
Review – Asymmetric Rh Chemistry

Cyclopentane Synthesis (D. O’Malley – Baran Group Meeting)

4+3 cycloadditions in Synthesis (Evans group seminar)

Andrew G Meyers Chem 115 web page (link)
Asymmetric Allylation Handout (pdf)
Stereoselective Aldol Reactions
Oxidation
Sharpless epoxidation
Jacobsen epoxidation
Shi epoxidation
Asymmetric Dihydroxylation
Asymmetric Epoxidation combined file
Noyori Asymmetric Hydrogenation
Reductions
Birch Reduction

Homework

Homework 1
Homework 2