Photoinduced Intramolecular Cyclization of Acylsilanes Bearing a Boronate Moiety: Construction of a Highly Strained <i>trans-</i>Fused Bicyclo[3.3.0]octane Skeleton
Photoinduced Intramolecular Cyclization of Acylsilanes Bearing a Boronate Moiety: Construction of a Highly Strained <i>trans-</i>Fused Bicyclo[3.3.0]octane Skeleton
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带有硼酸酯部分的酰基硅烷的光诱导分子内环化：高应变<i>反式</i>稠合双环[3.3.0]辛烷骨架的构建
DOI：
10.1021/acs.orglett.2c02337
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Kusama Hiroyuki
中科院分区：
文献类型：
--
作者：
Yamaguchi Kohei;Shimizu Tsukasa;Miura Arihito;Ishida Kento;Kusama Hiroyuki
利用含硼酸酯的酰基硅烷的光诱导环化反应，探索了一种可靠的构建反式稠合双环[n.3.0]骨架的策略。通过环烯烃衍生物的硼氢化反应制备了具有1，2-反式关系的酰基硅烷和硼酸酯的底物。通过光辐射有效地促进了环化反应，得到了作为单一非对映异构体的反式稠合双环[n.3.0]衍生物。值得注意的是，这种方法能够有效地构建高度应变的反式-5-5环系统。
A reliable strategy for the construction oftrans-fused bicyclo[n.3.0] skeletons was explored by utilizing photoinduced cyclization of acylsilanes bearing a boronate. The substrates having an acylsilane and a boronate in a 1,2-transrelationship were prepared via hydroboration of cycloalkene derivatives. The desired cyclization was efficiently promoted by photoirradiation to give thetrans-fused bicyclo[n.3.0] derivatives as a single diastereomer. It is noteworthy that this methodology enables the efficient construction of a highly strainedtrans-5-5 ring system.