Department of Chemistry, Wake Forest University, P.O. Box 7486, Winston-Salem, North Carolina 27109, USA.
J Org Chem. 2010 Dec 3;75(23):8155-65. doi: 10.1021/jo1017734. Epub 2010 Nov 11.
An ene-yne cross methasis of silyl-substituted alkynes and alkenes has been developed as a route to 4-aryl- and 4-alkyl-2-silyl-substituted 1,3-dienes. The dienes prepared were used to affect highly diastereoselective Diels-Alder reactions and then the silicon-substituted Diels-Alder cycloadducts were used in Hiyama cross-coupling reactions. The cross-coupling reactions enable these silicon dienes to be used as synthons for a variety of other dienes one might prepare and need access to. Two of the silicon-substituted Diels-Alder cycloadducts and one of the Hiyama cross-coupling products were also characterized by X-ray crystallography.
已开发出一种硅取代炔烃和烯烃的 ene-yne 交叉甲基化反应途径，作为合成 4-芳基和 4-烷基-2-硅取代 1,3-二烯的方法。制备的二烯可用于影响高度非对映选择性的 Diels-Alder 反应，然后将硅取代的 Diels-Alder 环加成物用于 Hiyama 交叉偶联反应。这些交叉偶联反应使这些硅二烯能够作为各种其他可能制备和需要获得的二烯的合成子使用。通过 X 射线晶体学还对两个硅取代的 Diels-Alder 环加成物和一个 Hiyama 交叉偶联产物进行了表征。
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