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

An Organizational Format for the Classification of Functional Groups. Applications to the Construction of Difunctional Relationships

Leading References: Langer, P. Angew. Chem. Int. Ed. Engl. 2000, 39, 3049-3052. Ciganek, E. Org. React. 1997, 51, 201-350. Basavaiah, D.; et. al. Tetrahedron, 1996, 52, 8001-8062. Drewes, S. E.; Roos, G. H. P. Tetrahedron, 1988, 44, 4653-4670

Other Useful References Polyketide Biosynthesis Historical Perspective on the Aldol Reaction Aldol Diastereoselectivity Enolate Diastereoface Selectivity Absolute Control in the Aldol Process

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)

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

Enantioselective Carbonyl Addition Handout

Tautomerism in C=O and C=NR Systems C=O Enolization with Metal Amide Bases C=O Enolization: Kinetic Acidities Mild Methods for Enolate Generation Enolate Structure: A Survey of X-ray Structures