Chemistry 206 Advanced Organic Chemistry Handout 27A Vicinal Elimination Reactions: An Overview Matthew D. Shair Wednesday

Sulfur-Based Activating Groups Sulfur-Ylides Sulfur-Stabilized Carbanions: Structure Sulfone-Based Transformations Pummerer Rearrangement

Krista Beaver Synthetic Applications of α-Diazocarbonyl Derivatives Chem 206 Synthetic Applications of α-Diazocarbonyl Compounds An Evans Group Afternoon Seminar Krista Beaver January 15, 1999 Leading References:

Nitro and Diazo Groups Historical Perspective Charge Affinity Patterns Functional Group Classification Scheme The Chemistry of the –NO2 Group

Double Stereodifferentiating Aldol Reactions The Mukaiyama Aldol Reaction Variant Allylmetal Nucleophiles as Enolate Synthons

Relevant Background Reading Chemistry 206 Advanced Organic Chemistry Lecture Number 28 Ambiphilic Functional Groups–3

D. Seebach Angew. Chem. Int. Ed. Engl., 27, 1624 (1983). (handout) \Stereoselective Alkylation Reactions of Chiral Metal Enolates\. D. A. Evans Asymmetric Synthesis, 3, 1 (1984). (handout)

Supplemental Enantioselective Carbonyl Addition Handout Matthew D. Shair Wednesday

eactions of Carbon Nucleophiles with Carbonyl Compounds Carey & Sundberg: Part B; Chapter 5 Reduction of Carbonyl & Other Functional Groups

Construct a model for the addition process in eq 1 using the principles learned thus far in the course