Synthesis 2005(13): 2091-2115  
DOI: 10.1055/s-2005-872084
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Boron-Substituted Building Blocks in Diels-Alder and Other Cycloaddition Reactions

Gerhard Hilt*, Patrick Bolze
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: Hilt@chemie.uni-marburg.de;
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Publikationsverlauf

Received 4 March 2005
Publikationsdatum:
20. Juli 2005 (online)

Abstract

Boron-containing building blocks are among the most prominent starting materials in several transformations based on their wide range of synthetic applications. Over the last decade various cycloaddition reactions were reported where boron-containing 1,3-dienes or boron-containing dienophiles were used. Combined with the broad follow-up chemistry, target-oriented as well as diversity-oriented syntheses could be established.

  • 1 Introduction

  • 2 Boron-Functionalised 1,3-Dienes

  • 2.1 Boron in Position 1

  • 2.2 Boron in Position 2

  • 3 Boron-Functionalised Dienophiles

  • 3.1 Alkenyl Boron Reagents

  • 3.2 Alkynyl Boron Reagents

  • 4 Boron Reagents in 1,3-Dipolar Cycloaddition

  • 5 Miscellaneous

  • 6 Outlook

77

Early calculations on a RHF/3-21G level were consistent with the observed chemical behavior; compare ref. 76.