3_16_05 - V. Catalytic Methods Background Topics for...

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Massachusetts Institute of Technology Organic Chemistry 5.512 March 16, 2005 Prof. Rick L. Danheiser Unit 2 Stereocontrolled Alkylation and Related Electrophilic Substitution Strategies Key Retrons R Z R 1 O * R Z X O * O R, X * R Z R 1 O * R 2 R Z R 1 O * X I. Intrinsic Stereochemistry II. Substrate Control: Asymmetric Induction by Molecular Framework III. Substrate Control: Asymmetric Induction by Chiral Auxiliaries IV. Reagent Control Strategies: Chiral Electrophiles
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Unformatted text preview: V. Catalytic Methods Background Topics for Review: Conditions for generating enolates, "azaenolates", and related species; pK A of relevant substrates and bases, kinetic vs. thermodynamic conditions for enolate generation, enolate stereochemistry, relative reactivity of alkylating agents, conditions for imine and hydrazone formation and cleavage, synthetically useful transformations of carbonyl compounds....
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