Cyclization Reactions of 1,3-Bis-Silyl Enol Ethers and Related Masked Dianions

Peter Langer

doi:10.1055/s-2002-20954

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Synthesis 2002(4): 0441-0459
DOI: 10.1055/s-2002-20954

REVIEW

Cyclization Reactions of 1,3-Bis-Silyl Enol Ethers and Related Masked Dianions

Peter Langer*^a,b
^a Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstr. 2, 37077 Göttingen, Germany
Fax: +49(551)399475; e-Mail: planger@gwdg.de;
^b Current address: Institut für Chemie und Biochemie der Ernst-Moritz-Arndt Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany

Further Information

Publication History

Received 12 November 2001
Publication Date:
28 July 2004 (online)

Abstract
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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.

1 Synthesis and Rearrangements of 1,3-Bis-Silyl Enol Ethers
2 Aldehydes and Ketones
3 Acetals
4 1,2-Dicarbonyl Derivatives
5 1,3-Dicarbonyl Derivatives
6 Orthoesters
7 1,4-Dicarbonyl Derivatives
8 Carboxylic Acid Derivatives
9 Oxalyl Chloride
10 Epoxides
11 Michael Reactions
12 [4+2] Cycloadditions
13 SET Reactions

Key words

1,3 dicarbonyl dianions - 1,3-bis-silyl enol ethers - SET reactions - Michael reactions - cyclizations

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Langer, P.; Albrecht, U. manuscript in preparation.