Organic Syntheses via Boranes Vol. 2, H.C. Brown

General description

Provides an account of recent developments in organoborane chemistry. Topics include Hydroboration with Borane, and with Borane Derivatives, Organoborane Conversions to Functional Groups, and Carbon-Carbon Bond Formation via Organoboranes. Each survey chapter is followed by a chapter providing detailed experimental procedures.

Table of Contents

1 Hydroboration with Borane: Survey
1.1 General Comments
1.2 Borane Adducts for Hydroboration
1.3 Scope, Stoichiometry, and Mechanism
1.4 Directive Effects
1.5 Stereochemistry of Hydroboration
1.6 Hydroboration of Dienes, Trienes, and Acetylenes
1.7 Hydroboration of Functional Derivatives
2 Hydroboration with Borane: Procedures

3 Hydroboration with Borane Derivatives: Survey
3.1 Monosubstituted Boranes
3.2 Disubstituted Boranes
3.3 Catalytic Hydroboration
3.4 Asymmetric Hydroborating Agents
3.5 Catalytic Asymmetric Hydroboration
4 Hydroboration with Borane Derivatives: Procedures

5 Organoborane Conversions to Functional Groups: Survey
5.1 Thermal Isomerization and Displacement
5.2 Protonolysis
5.3 Oxidation
5.4 Amination
5.5 Halogenolysis
5.6 Transmetalation from Boron
6 Organoborane Conversions to Functional Groups: Procedures

7 Carbon-Carbon Bond Formation Via Organoboranes: Survey
7.1 Organoborate Rearrangements
7.2 Versatile Organoboranes
7.3 Allylboration, Allenylboration, and Propargylboration
7.4 General Asymmetric Synthesis Based on Asymmetric Hydroboration and Asymmetric Homologation
7.5 Asymmetric Allylboration, Allenylboration, and Propargylboration
7.6 Enolboration
7.7 The Diels-Alder Reaction
7.8 The Cross-Coupling Reaction
8 Carbon-Carbon Bond Formation Via Organoboranes: Procedures

9 Boron NMR as a Tool for Organic Chemistry
9.1 Hydroboration Reaction
9.2 Cleavage of Ether Using IpcBBr₂
9.3 Asymmetric Reduction of Acetophenone with DIP-Chloride™
9.4 Unexpected Asymmetric Reduction Reactions.
9.5 Unexpected Reactions of alpha-Diketones.
9.6 ¹¹B NMR Spectrum of Equilibrium Mixtures.
9.7 Asymmetric Allylboration of Benzaldehyde with B-Allyldiisopinocampheylborane
Table 9.2 ¹¹B NMR Chemical Shifts
Scheme 9.1 ¹¹B NMR Shifts Relative to BF₃:OEt₂
Index