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Issue 15, 2011
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Silyl-substituted 1,3-butadienes for Diels–Alder reaction, ene reaction and allylation reaction

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Abstract

Silyl-substituted 1,3-butadienes are useful building blocks and are readily applied in several types of reactions such as Diels–Alder reaction, ene reaction and allylation. They can also participate in different tandem reactions such as Diels–Alder/allylation, ene/allylation, ene/allylation/Diels–Alder reaction, ene/allylation/ene reaction and ene/allylation/Diels–Alder/allylation reaction. This feature article reviews the synthesis of silyl-substituted 1,3-butadienes, and their applications in the reaction types mentioned above, involving a tandem Diels–Alder/ene/allylation process. This article also introduces some reactions of alkenylsilanes and allylsilanes for comparison and discussion about the tandem reaction. The tandem reactions described in this article are a powerful tool to construct complicated multicyclic compounds with high selectivity and high efficiency.

Graphical abstract: Silyl-substituted 1,3-butadienes for Diels–Alder reaction, ene reaction and allylation reaction

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Publication details

The article was received on 19 Dec 2010, accepted on 28 Jan 2011 and first published on 21 Feb 2011


Article type: Feature Article
DOI: 10.1039/C0CC05665K
Citation: Chem. Commun., 2011,47, 4348-4357
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    Silyl-substituted 1,3-butadienes for Diels–Alder reaction, ene reaction and allylation reaction

    F. Zhao, S. Zhang and Z. Xi, Chem. Commun., 2011, 47, 4348
    DOI: 10.1039/C0CC05665K

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