2_28_05 - Dipole-dipole interactions II Tactics for...

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Massachusetts Institute of Technology Organic Chemistry 5.512 February 28, 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 Deviation from optimal geometry for orbital overlap (angle strain) Destabilizing torsional interactions Stabilizing secondary orbital interactions
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Unformatted text preview: Dipole-dipole interactions II. Tactics for establishing thermodynamic control Reading on Stereochemical Principles Carey and Sundberg "Advanced Organic Chemistry" Part A (2000) Chapters 2 and 3 E. L. Eliel and S. H. Wilen "Stereochemistry of Organic Compounds" (1994) Review of Key Reactions Carey and Sundberg "Advanced Organic Chemistry" Part B (2000) Chapter 1 (Alkylation reactions) Chapter 2 (Aldol, Michael, Mannich reactions) Chapter 4 (Hydroboration) Chapter 9 (Organoboron, silicon, tin chemistry) Chapter 12 (Epoxidation)...
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