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)

La3(Ot-Bu)9 (3.3 mol%), -72° C, 30 h, 74% yield Y3(Ot-Bu)8Cl (3.3 mol%), -43° C, 3.5 h, 50% yield Zr(Ot-Bu)4 (140 mol%), -50° C, 2.5 h, 86% yield La3(Ot-Bu)9 (3.3 mol%)

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

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

Enantioselective Carbonyl Addition Handout