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Photoinduced Intramolecular Cyclization of Acylsilanes Bearing a Boronate Moiety: Construction of a Highly Strained trans-Fused Bicyclo[3.3.0]octane Skeleton
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.orglett.2c02337
Kohei Yamaguchi 1 , Tsukasa Shimizu 1 , Arihito Miura 1 , Kento Ishida 1 , Hiroyuki Kusama 1
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A reliable strategy for the construction of trans-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-trans relationship were prepared via hydroboration of cycloalkene derivatives. The desired cyclization was efficiently promoted by photoirradiation to give the trans-fused bicyclo[n.3.0] derivatives as a single diastereomer. It is noteworthy that this methodology enables the efficient construction of a highly strained trans-5-5 ring system.

中文翻译:

带有硼酸酯部分的酰基硅烷的光诱导分子内环化:高应变反式稠合双环[3.3.0]辛烷骨架的构建

通过利用带有硼酸盐的酰基硅烷的光诱导环化,探索了构建反式稠合双环[ n.3.0 ]骨架的可靠策略。通过环烯烃衍生物的硼氢化制备具有1,2-反式关系的酰基硅烷和硼酸盐的基材。通过光辐照有效地促进了所需的环化,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。
更新日期:2022-08-03
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