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

Reading Assignment for week Olefin Addition Reactions: Part–3 Chemistry 206 Advanced Organic Chemistry

Hoffmann, Angew. Chem. Int. Ed. 1979, 18, 563-572 (Stereochemistry of) Nakai, Chem. Rev. 1986, 86, 885-902 (Wittig Rearrangement) Evans, Accts. Chem. Res. 1974, 7, 147-55 (Sulfoxide Rearrangement)

Woodward-Hoffmann Theory R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970. Frontier Molecular Orbital Theory I. Fleming, Frontier Orbitals and Organic Chemical Reactions

Advanced Organic Chemistry Handout–10A Diastereoselective Attack of Electrophiles on Chiral Olefins Matthew D. Shair Wednesday