3_02_05 - Kinetic Control Relative energy of diastereomeric...

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Massachusetts Institute of Technology Organic Chemistry 5.512 March 2, 2005 Prof. Rick L. Danheiser Introduction: Strategies for Stereocontrolled Synthesis Thermodynamic Control Relative energy of diastereomers determines outcome of reaction I. What determines the relative energy of stereoisomers? De-stabilizing Non-bonded Repulsion Stabilizing Non-covalent Interactions Stereoelectronic Effects II. Tactics for establishing thermodynamic control
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Unformatted text preview: Kinetic Control Relative energy of diastereomeric transition states determines outcome Substrate Control Steric Approach Control Stereoelectronic Control Internal Stereodirection Reagent Control Achiral Substrate: enantiotopic face selectivity Achiral Substrate: enantiotopic group selectivity Chiral Substrate: double asymmetric synthesis Dynamic Kinetic Resolution...
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