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多组分可见光驱动光催化促进的 -杂螺环的直接组装。

Multicomponent Direct Assembly of -Heterospirocycles Facilitated by Visible-Light-Driven Photocatalysis.

机构信息

Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.

出版信息

J Org Chem. 2022 Oct 7;87(19):13204-13223. doi: 10.1021/acs.joc.2c01684. Epub 2022 Sep 14.

Abstract

-heterospirocycles are interesting structural units found in both natural products and medicinal compounds but have relatively few reliable methods for their synthesis. Here, we enlist the photocatalytic generation of -centered radicals to construct β-spirocyclic pyrrolidines from -allylsulfonamides and alkenes. A variety of β-spirocyclic pyrrolidines have been constructed, including drug derivatives, in moderate to very good yields. Further derivatization of the products has also been demonstrated as has a viable scale-up procedure, making use of flow chemistry techniques.

摘要

杂螺环是天然产物和药物化合物中都存在的有趣结构单元,但它们的合成方法相对较少。在这里,我们利用光催化生成中心自由基,从 -烯丙基磺酰胺和烯烃构建β-螺环吡咯烷。构建了多种β-螺环吡咯烷,包括药物衍生物,产率中等至非常好。还展示了产物的进一步衍生化,以及使用流动化学技术的可行放大程序。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32b6/9552240/ff6c2cc2c148/jo2c01684_0002.jpg

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