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DOI: 10.1055/s-2006-958958
One-Pot Synthesis of Functionalized Carbacycles by Formal [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Dielectrophiles
Publikationsverlauf
Publikationsdatum:
21. Dezember 2006 (online)
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Abstract
Lewis acid mediated [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, such as 1,1,3,3-tetramethoxypropane, 3-silyloxy-2-en-1-ones and 1,1-diacylcyclopropanes, provide an efficient approach to a variety of functionalized arenes (such as salicylates and phenols) and other six-membered carbacyclic products.
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1 Introduction
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2 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Bis(acetals)
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3 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Ketoacetals and 1,3-Keto-S,O-acetals
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4 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Alkoxy-2-en-1-ones and 3-Silyloxy-2-en-1-ones
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4.1 Preparative Scope
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4.2 Synthetic Applications
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5 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,1-Diacylcyclopropanes
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6 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,1-Diacylcyclopentanes
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7 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Oxoalkanoic acid derivatives
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8 [3+3] Cyclizations of 1-Silyloxy-1-alkoxy-3-arylthiobuta-1,3-dienes, 1,3-Dialkoxy-1-silyloxybuta-1,3-dienes and 1-Silyloxy-1-alkoxy-3-aryloxybuta-1,3-dienes
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9 Conclusions
Key words
arenes - cyclization - one-pot reaction - salicylic acid - silyl enol ethers
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References
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15Höttecke, N.; Fischer, C.; Reinke, H.; Langer, P. unpublished results.
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