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Organoboranes for Syntheses

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This book examines the recent advances in the art of organic synthesis via organoboranes. The volume includes a wide range of topics in asymmetric synthesis, such as reduction,
aldol reaction, allyboration, homologation, and cyclopropanation. Additional subjects include Suzuki coupling, amino acid synthesis, fluoro-organic synthesis,
boron catalysts for stereoselective transformations,
heterocyclic synthesis and novel borohydride reagents.
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Editorial Reviews

The 16 papers, from an August 1999 symposium in New Orleans, summarize the state of organoborane chemistry for organic synthesis. The methods they describe are stoichiometric, catalytic, and asymmetric and synthesis. The topics include the synthesis and cyclizations of conjugated system derived from organoboranes, cross-coupling reactions of organoboron compounds with organic eletrophile, arylboron catalysts for stereoselective organic transformations, asymmetric aldol reactions using boron enolates and their application to polyketide synthesis, and the syntheses of chiral lactones with asymmetric allylboration. The collection is primarily for organic chemists in academia or industry, but can be adapted for use in a graduate course in organoborane or synthetic organic chemistry. Annotation c. Book News, Inc., Portland, OR (
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Product Details

  • ISBN-13: 9780841237087
  • Publisher: American Chemical Society
  • Publication date: 3/28/2001
  • Series: ACS Symposium Series , #783
  • Pages: 264
  • Product dimensions: 5.90 (w) x 8.80 (h) x 0.80 (d)

Table of Contents

1 Recent Advances in Borane Chemistry 1
2 Lithium Aminoborohydrides: Reagents with Multiple Personalities 18
3 New Stereoselective Transformations Involving Organoboranes and Organozinc Compounds: Applications of the Boron-Zinc Chain Reaction and the Diastereoselective Migration of Organoboranes 33
4 Synthesis and Cyclizations of Conjugated Systems Derived from Organoboranes 52
5 New Organic Synthetic Methods Using the NaBH[subscript 4]/I[subscript 2] System 65
6 Cross-Coupling Reaction of Organoboron Compounds with Organic Electrophiles 80
7 Rhodium-Catalyzed Addition Reactions of Organoboronic Acids 84
8 Arylboron Catalysts for Stereoselective Organic Transformations 108
9 Asymmetric Reduction of [alpha]-Functionalized Ketones with Organoboron-Based Chiral Reducing Agents 122
10 Enantioselective Cyclopropanation Using Dioxaborolane Ligands 136
11 Organoboron Chemistry on Alumina: The Suzuki Reaction 148
12 Synthesis of Heterocyclic Compounds by Allylboration Reactions 160
13 Novel Silyl-Mediated 10-TMS-9-BBD Organoborane Reagents for Asymmetric Synthesis 176
14 Asymmetric Aldol Reactions Using Boron Enolates: Applications to Polyketide Synthesis 195
15 Recent Progress in Asymmetric Synthesis with Boronic Esters 207
16 Syntheses of Chiral Lactones via Asymmetric Allylboration 220
Author Index 235
Subject Index 236
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