Tetrahedron

Diels-Alder reaction of α-substituted acrylates and α-(methylene) lactones: Conformation of dienophiles and endo/exo selectivity

K Takeda, I Imaoka, E Yoshii

文献索引：Takeda, Kei; Imaoka, Ikuhiro; Yoshii, Eiichi Tetrahedron, 1994 , vol. 50, # 37 p. 10839 - 10848

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被引用次数: 30

摘要

Diels-Alder reaction of 1, 6-bis (trimethylsilyloxy)-2, 4-hexadiene with α-substituted acrylates and 5 to 7-and 9 to 11-membered α-(methylene) lactones has been carried out to examine correlation of dienophile structure with endo/exo selectivity. While the conformationally flexible acrylates produced cycloadducts of endo/exo= 59: 41 to 74: 26, the 5 to 7-membered lactones with rigid s-cis conjugate system provide cyloadducts of endo/exo= 13: 87 to 32: ...