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Teaching GuideTerm Faculty of Science |
| Mestrado Universitario en Investigación Química e Química Industrial (Plan 2020) |
 Subjects |
| Stereoselective Synthesis |
| Contents |
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| Identifying Data | 2020/21 | |||||||||||||
| Subject | Stereoselective Synthesis | Code | 610509113 | |||||||||||
| Study programme |
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| Descriptors | Cycle | Period | Year | Type | Credits | |||||||||
| Official Master's Degree | 1st four-month period |
First | Optional | 3 | ||||||||||
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| Topic | Sub-topic |
| Chapter 1. Stereochemistry in chemical reactions. Conformational control of stereoselectivity | Chirality. Stereogenic units. Topicity. Diastereoselectivity and enantioselectivity. The “chiral pool”: chiral auxiliaries and chiral ligands. Kinetic resolution. Conformational control of the diastereoselectivity. Stereoelectronic effects. The Curtin-Hammett principle. |
| Chapter 2. Additions to C=C trigonal centers | Additions to C=C bonds. Diastereoselective epoxidations of acyclic and cyclic olefins. Enantioselective epoxidations (Sharpless, Jacobsen, Shi). Synthetic applications of epoxyalcohols. Diastereoselective dihydroxylations of acyclic and cyclic olefins. Sharpless enantioselective dihydroxylation (SAD). Sharpless enantioselective aminohydroxylation (SAA). Diastereoselective olefin hydrogenation. Enantioselective hydrogenation |
| Chapter 3. Additions to C=O trigonal centers. | Addition to C=X bonds. Sterecontrol in nucleophilic additions to carbonyl groups in acyclic and cyclic compounds. 1,2 and 1,3-Asymmetric induction models. Enantioselective additions to ketones. Nucleophilic additions to imines and sulfinamides. |
| Chapter 4. Conjugate additions to C=C-C=X systems | Conjugate additions to C=C-C=O systems. Diastereoselective conjugate additions. Catalytic asymmetric conjugate additions. Reduction of conjugated systems. Asymmetric epoxidation of enones. |
| Chapter 5. Additions to C=C-X systems | Additions to C=C-OM bonds. Regio- y stereoselective synthesis of enolates. Diastereoselective reactions of chiral enolates: alkylation, halogenation, amination and hydroxilation. Diastereoselective reactions of chiral azaenolates |
| Chapter 6. Reactions between trigonal centers | Reactions between trigonal centers: generation of two or more stereocenters. Aldol reaction: control of the diastereoselectivity. The Zimmerman-Traxler model. Organocatalyzed aldol reactions. Aldol Mukaiyama reaction of latent enolates. Double diastereoselection: chiral centers on the components of the aldol reaction. Addition of allyl organometals to carbonyl groups. Allylic boranes. Allylic stannanes and silanes: catalysis by chiral Lewis acids and bases. Addition of allyl organometals to imines. Diastereoselectivity in Diels-Alder cycloadditions |
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