Synthesis 2007(3): 327-347  
DOI: 10.1055/s-2006-958958
REVIEW
© Georg Thieme Verlag Stuttgart · New York

One-Pot Synthesis of Functionalized Carbacycles by Formal [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Dielectrophiles

Holger Feista, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: [email protected];
b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 29 May 2006
Publication Date:
21 December 2006 (online)

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.

  • 1 Introduction

  • 2 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Bis(acetals)

  • 3 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,3-Ketoacetals and 1,3-Keto-S,O-acetals

  • 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

  • 4.1 Preparative Scope

  • 4.2 Synthetic Applications

  • 5 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,1-Diacylcyclopropanes

  • 6 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 1,1-Diacylcyclopentanes

  • 7 [3+3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Oxoalkanoic acid derivatives

  • 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

  • 9 Conclusions

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5

Ahmed, Z.; Büttner, S.; Sher, M.; Trabhardt, T.; Langer, P. unpublished results.

15

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16

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