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DOI: 10.1055/s-2002-20954
Cyclization Reactions of 1,3-Bis-Silyl Enol Ethers and Related Masked Dianions
Publication History
Publication Date:
28 July 2004 (online)
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Abstract
Despite their simplicity and synthetic usefulness, reactions of 1,3-dicarbonyl dianions are often problematic, since they represent highly reactive compounds (low reactivity matching). In addition, functionalized electrophiles are often rather labile and reactions with strong nucleophiles can result in polymerisation, decomposition, formation of open-chain products, elimination, or SET-reactions. These intrinsic limitations can be overcome by the use of 1,3-bis-silyl enol ethers, electroneutral 1,3-dicarbonyl dianion equivalents, in Lewis acid catalyzed reactions.
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1 Synthesis and Rearrangements of 1,3-Bis-Silyl Enol Ethers
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2 Aldehydes and Ketones
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3 Acetals
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4 1,2-Dicarbonyl Derivatives
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5 1,3-Dicarbonyl Derivatives
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6 Orthoesters
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7 1,4-Dicarbonyl Derivatives
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8 Carboxylic Acid Derivatives
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9 Oxalyl Chloride
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10 Epoxides
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11 Michael Reactions
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12 [4+2] Cycloadditions
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13 SET Reactions
Key words
1,3 dicarbonyl dianions - 1,3-bis-silyl enol ethers - SET reactions - Michael reactions - cyclizations
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