Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, 3012, Bern, Switzerland.
CEISAM UMR CNRS 6230-UFR des Sciences et des Techniques, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.
Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13329-13332. doi: 10.1002/anie.201707791. Epub 2017 Sep 25.
An efficient and simple radical chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves a radical addition-translocation-cyclization process and necessitates solely the use of readily available arenesulfonyl chlorides in tetrahydrofuran. Interestingly, this radical-mediated C-H activation process took place with a high level of retention of configuration when an enantiomerically pure starting material was used.
描述了一种将末端炔烃转化为芳磺酰甲基环戊烷的高效、简单的自由基链反应。该反应涉及自由基加成-迁移-环化过程,仅需在四氢呋喃中使用易得的芳磺酰氯。有趣的是,当使用手性纯起始原料时,这种自由基介导的 C-H 活化过程具有高度的构型保持。