Carbonyl and Azomethine Electrophiles-1 Relevant Dunitz Articles Geometrical Reaction Coordinates. Il. Nucleophilic Addition to Reactivity Trends

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

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

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

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

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)

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