E. Vedejs – Lewis Base Catalysis in Organic Synthesis (2016)

Автор: E. Vedejs
Название книги: Lewis Base Catalysis in Organic Synthesis (2016)
Формат: PDF
Жанр: Химия
Страницы: 1441
Качество: Изначально компьютерное, E-book

This three-volume set represents the first comprehensive coverage of the rapidly expanding field of Lewis base catalysis that has attracted enormous attention in recent years. Lewis base catalysis is a conceptually novel paradigm that encompasses an extremely wide variety of preparatively useful transformations and is particularly effective for enantioselectively constructing new stereogenic centers. As electron-pair donors, Lewis bases can influence the rate and stereochemical course of myriad synthetic organic reactions. The book presents the conceptual/mechanistic principles that underlie Lewis base catalysis, and then builds upon that foundation with a thorough presentation of many different reaction types. And last but not least, the editors, Prof. Edwin Vedejs and Prof. Scott E. Denmark, are without doubt the leaders in this emerging field and have compiled high quality contributions from an impressive collection of international experts.
Contents
Volume 1
From Catalysis to Lewis Base Catalysis with Highlights from 1806 to 1970
Principles
Principles, Definitions, Terminology, and Orbital Analysis of Lewis Base–Lewis Acid Interactions Leading to Catalysis
Thermodynamic Treatments of Lewis Basicity
Quantitative Treatments of Nucleophilicity and Carbon Lewis Basicity
Mechanism and Lewis Base Catalysis: Nucleophilicity Is Only Part of the Story
Anhydride Activation by 4-Dialkylaminopyridines and Analogs (n – π*)
Mechanistic Understanding of Proline Analogs and Related Protic Lewis Bases (n – π*)
Mechanistic Options for the Morita–Baylis–Hillman Reaction (n – π*)
Mechanism of C-Si Bond Cleavage Using Lewis Bases (n – σ*)
Bifunctional Lewis Base Catalysis with Dual Activation of X3Si-Nu and C=O (n – σ*)
Bifunctional Lewis Base Catalysis with Dual Activation of R–M and C=O (n – σ*)
The Corey–Bakshi–Shibata Reduction: Mechanistic and Synthetic Considerations – Bifunctional Lewis Base Catalysis with Dual Activation
Volume 2
Applications: Lewis Base Catalysis Involving an n – π* Activation Step
Chiral Lewis Base Activation of Acyl and Related Donors in Enantioselective Transformations
(n – π*)
Catalytic Generation of Ammonium Enolates and Related Tertiary Amine-Derived Intermediates: Applications, Mechanism, and Stereochemical Models (n – π*)
Morita–Baylis–Hillman, Vinylogous Morita–Baylis–Hillman, and Rauhut–Currier Reactions
Beyond the Morita–Baylis–Hilman Reaction (n – π*)
Iminium Catalysis (n – π*)
Enamine-Mediated Catalysis (n – π*)
Volume 3
Applications: Enhanced Nucleophilicity by Lewis Base Activation (n – σ*, n – n*)
Si-C-X and Si-C-EWG as Carbanion Equivalents under Lewis Base Activation (n – σ*)
Activation of B-B and B-Si Bonds and Synthesis of Organoboron and Organosilicon Compounds through Lewis Base-Catalyzed Transformations (n – n*)
Applications: Enhanced Electrophilicity and Dual Activation by Lewis Base Catalysis (n – σ*)
Lewis Base-Catalyzed Reactions of SiX 3 -Based Reagents with C=O, C=N (n – σ*)
Lewis Base-Catalyzed, Lewis Acid-Mediated Reactions (n – σ*)
Lewis Bases as Catalysts in the Reduction of Imines and Ketones with Silanes (n – σ*)
Reactions of Epoxides (n – σ*)
Lewis Base-Catalyzed Generation of Electrophilic Intermediates
Lewis Base Catalysis: A Platform for Enantioselective Addition to Alkenes Using Group 16
and 17 Lewis Acids (n – σ*)
Bifunctional (and Multifunctional) Catalysis
Bifunctional and Synergistic Catalysis: Lewis Acid Catalysis and Lewis Base-Assisted Bond
Polarization (n – σ*)
Bifunctional Catalysis with Lewis Base and X-H Sites That Facilitate Proton Transfer or Hydrogen Bonding (n – π*)
Carbenes: Lewis Base Catalysis Triggers Multiple Activation Pathways