Silyl-substituted 1,3-butadienes for Diels-Alder reaction, ene reaction and allylation reaction.

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, China 100871.

Chemical communications (Cambridge, England) 2011 Apr 21

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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. © The Royal Society of Chemistry 2011

Citation

Fei Zhao, Shaoguang Zhang, Zhenfeng Xi. Silyl-substituted 1,3-butadienes for Diels-Alder reaction, ene reaction and allylation reaction. Chemical communications (Cambridge, England). 2011 Apr 21;47(15):4348-57