Stereodirected Synthesis with Organoboranes

"...this is the type of book that could only be written by a scholar who has devoted many years to organoboron chemistry. Matteson has done it, and done it well." - Synthesis

• 1 Introduction to Borane Chemistry.- 1.1 Beginnings.- 1.2 Structure and Bonding in Organoboranes.- 1.3 General Chemical Properties of Organoboranes.- 1.4 Safety Considerations.- 1.5 References.- 2 Sources of Compounds Containing Boron—Carbon Bonds.- 2.1 Industrial Sources of Boron Compounds.- 2.2 The Organometallic Route.- 2.3 Hydroboration.- 2.4 Haloborations.- 2.5 Other Routes to Carbon—Boron Bonds.- 2.6 References.- 3 General Reactions of Organoboranes.- 3.1 Introduction.- 3.2 Oxidative Replacement of Boron.- 3.3 Boron Substituted Carbanions.- 3.4 Replacement of Boron by Carbon.- 3.5 Reactions at Sites Other than the B-C Bond.- 3.6 References.- 4 Alkenylboranes and Control of Olefinic Geometry.- 4.1 Introduction.- 4.2 ?-Elimination Routes to Unsaturated Compounds.- 4.3 The Suzuki Coupling Reaction.- 4.4 Other Stereoselective Routes to Alkenes.- 4.5 References.- 5 Asymmetric Synthesis via (a-Haloalkyl)boronic Esters.- 5.1 Introduction.- 5.2 Synthetic Methodology: Pinanediol Esters.- 5.3 Synthetic Methodology: Chiral Directors Having C2 Symmetry.- 5.4 Synthetic Applications.- 5.5 References.- 6 Asymmetric Hydroboration Chemistry.- 6.1 Introduction.- 6.2 Asymmetric Hydroboration.- 6.3 Transformations of Asymmetric Organoboranes.- 6.4 Substrate Directed Hydroboration.- 6.5 Catalytic Asymmetric Hydroboration.- 6.6 References.- 7 Allylboron and Boron Enolate Chemistry.- 7.1 Introduction.- 7.2 Allylic Boronic Esters.- 7.3 Allyldialkylboranes.- 7.4 Boron Enolates.- 7.5 References.- 8 Diels-Alder Reactions.- 8.1 Introduction.- 8.2 Alkenylboranes.- 8.3 Butadienylboranes.- 8.4 Catalyzed Diels-Alder Reactions.- 8.5 References.- 9 Asymmetric Reductions and Miscellaneous Reactions.- 9.1 Introduction.- 9.2 Reductions with Alkylboranes.- 9.3 Reductions with Asymmetric B-HCompounds.- 9.4 Other Borane Catalyzed Reactions.- 9.5 Asymmetric Hydrozirconation.- 9.6 References.- Author Index.