This monograph has been written to demonstrate to organic chemists and graduate students the strategies for controlling sterochemistry in carbon-carbon bond formations with borane intermediates. The boranes were initially found to be useful reagents by Nobel Laureate H.C. Brown. Their precursors are commercially available and derivatization is fast, clean and simple.

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.