Ueda Masafumi, Ito Yuta, Ichii Yuki, Kakiuchi Maiko, Shono Hiroko, Miyata Okiko
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558 (Japan), Fax: (+81)78-441-7554.
Chemistry. 2014 May 26;20(22):6763-70. doi: 10.1002/chem.201402217. Epub 2014 Mar 27.
A straightforward synthetic method for the construction of benzofuro[2,3-b]pyrrol-2-ones by a novel domino reaction through a radical addition/[3,3]-sigmatropic rearrangement/cyclization/lactamization cascade has been developed. The domino reaction of O-phenyl-conjugated oxime ether with an alkyl radical allows the construction of two heterocycles with three stereogenic centers as a result of the formation of two C-C bonds, a C-O bond, and a C-N bond in a single operation, leading to pyrrolidine-fused dihydrobenzofurans, which are not easily accessible by existing synthetic methods. Furthermore, asymmetric synthesis of benzofuro[2,3-b]pyrrol-2-one derivatives through a diastereoselective radical addition reaction to a chiral oxime ether was also developed.
通过自由基加成/[3,3]-σ迁移重排/环化/内酰胺化串联反应，开发了一种通过新型多米诺反应构建苯并呋喃[2,3-b]吡咯-2-酮的直接合成方法。O-苯基共轭肟醚与烷基自由基的多米诺反应，通过单次操作形成两个C-C键、一个C-O键和一个C-N键，从而构建出具有三个立体中心的两个杂环，得到吡咯烷稠合的二氢苯并呋喃，这是现有合成方法难以实现的。此外，还开发了通过对手性肟醚进行非对映选择性自由基加成反应来不对称合成苯并呋喃[2,3-b]吡咯-2-酮衍生物的方法。
