Modern Methods in Stereoselective Aldol ReactionsRainer Mahrwald John Wiley & Sons, 22 de fev. de 2013 - 548 páginas The selective formation of bondings between molecules is one of the major challenges in organic chemistry, and the so-called aldol reaction is one of the most important for this purpose. These reactions are a highly useful tool for developing such novel substances as natural products and pharmaceuticals. Likes its highly successful and much appreciated predecessor, "Modern Aldol Reactions", this ready reference provides a systematic overview of methodologies for installing a required configuration during an aldol addition step, but shifts the focus so as to cover the latest developments. As such, it presents a set of brand new tools, including vinylogous Mukaiyama-aldol reactions and substrate-controlled aldol reactions, as well as asymmetric induction in aldol additions. Furthermore, new developments in existing stereoselective aldol additions are described, such as the deployment of supersilyl groups or organocatalyzed aldol additions. All of these methodologies are presented in the context of their deployment in the total synthesis of natural products. |
Conteúdo
The Vinylogous Mukaiyama Aldol Reaction | 89 |
N OAcetals | 2-33 |
Chans Diene | 77 |
Organocatalyzed Aldol Reactions | 129 |
References | 3-85 |
Supersilyl Protective Groups in Aldol Reactions | 4 |
Asymmetric Induction in Aldol Additions | 25 |
Polypropionate Synthesis Via Substrate | 5-74 |
Application of Oxazolidinethiones | 7-11 |
References | 13 |
EnzymeCatalyzed Aldol Additions | 17 |
| 8-62 | |
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acetate acetone achieved active adduct affording aldol addition aldol products aldol reactions involving aldolases Angew application approach aromatic aldehydes asymmetric base bond boron catalyst catalyzed chelated Chem chiral aldehydes combination complex compound configuration corresponding cyclic derivatives diastereoface selectivity diastereomer diastereoselectivity effect enantioselectivities enolate entry equiv Evans examples excellent expected favor Figure formation formed fragment gave give highly induction interactions leading Lewis acid lithium matched methyl ketones mixture moderate Mukaiyama aldol reactions natural products nucleophile observed obtained OH OH OTBS Paterson performed prepared presence proline protecting protecting group relative reported respectively Scheme Q selectivity similar step stereocenter stereochemical stereocontrol stereoselective steric structure studies substrate synthesis synthetic Table Tetrahedron Lett total synthesis transformations transition VMAR yield