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Synthesis 2005(13): 2091-2115
DOI: 10.1055/s-2005-872084
DOI: 10.1055/s-2005-872084
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Boron-Substituted Building Blocks in Diels-Alder and Other Cycloaddition Reactions
Further Information
Received
4 March 2005
Publication Date:
20 July 2005 (online)
Publication History
Publication Date:
20 July 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.
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1 Introduction
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2 Boron-Functionalised 1,3-Dienes
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2.1 Boron in Position 1
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2.2 Boron in Position 2
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3 Boron-Functionalised Dienophiles
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3.1 Alkenyl Boron Reagents
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3.2 Alkynyl Boron Reagents
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4 Boron Reagents in 1,3-Dipolar Cycloaddition
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5 Miscellaneous
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6 Outlook
Key words
boron - cycloaddition - cyclotrimerisation - Diels-Alder reaction - 1,3-dipole
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References
Early calculations on a RHF/3-21G level were consistent with the observed chemical behavior; compare ref. 76.