Suzuki Itaru, Hamada Yu-Ya, Uji Yuki, Shibata Ikuya
Research Center for Environmental Preservation, Osaka University, 2-4 Yamadaoka, Suita, Osaka 565-0871, Japan.
Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.
Org Biomol Chem. 2022 Jul 13;20(27):5402-5405. doi: 10.1039/d2ob01096h.
Hydrostannylation of allenoate 1 with halogenotin hydride (BuSnClH) was developed to give allylic stannane (I), which then could react with aldehyde 2. The same coupling gave allylic alcohol 3 under reductive conditions in the presence of a silane and a catalytic amount of BuSnClH. This catalytic protocol was applied to the synthesis of lactone 4. The resultant products 3 and 4 were subjected to oxidative conditions to provide oxacycles 5 and 6, respectively.
利用卤化锡氢化物（BuSnClH）对烯丙酸酯1进行氢化锡化反应，得到烯丙基锡烷（I），然后其可与醛2发生反应。在硅烷和催化量的BuSnClH存在下，在还原条件下同样的偶联反应得到烯丙醇3。该催化方法应用于内酯4的合成。将所得产物3和4进行氧化处理，分别得到含氧杂环5和6。
