Nonn Melinda, Kiss Loránd, Haukka Matti, Fustero Santos, Fülöp Ferenc
Institute of Pharmaceutical Chemistry and ‡Stereochemistry Research Group of the Hungarian Academy of Sciences, University of Szeged , H-6720 Szeged, Eötvös u. 6, Hungary.
Org Lett. 2015 Mar 6;17(5):1074-7. doi: 10.1021/acs.orglett.5b00182. Epub 2015 Feb 16.
The selective introduction of fluorine onto the skeleton of an aminocyclopentane or cyclohexane carboxylate has been developed through a novel and efficient fluoride opening of an activated aziridine ring with XtalFluor-E. The reaction proceeded through a stereoselective aziridination of the olefinic bond of a bicyclic lactam and regioselective aziridine ring opening with difluorosulfiliminium tetrafluoroborate with the neighboring group assistance of the sulfonamide moiety to yield fluorinated diamino acid derivatives. The method based on the selective aziridine opening by fluoride has been generalized to afford access to mono- or bicyclic fluorinated substances.
通过用XtalFluor-E对活化氮丙啶环进行新颖且高效的氟开环反应，已实现将氟选择性引入氨基环戊烷或环己烷羧酸酯的骨架中。该反应通过双环内酰胺的烯键进行立体选择性氮丙啶化反应，以及在磺酰胺部分的邻基协助下用四氟硼酸二氟亚硫酰亚胺进行区域选择性氮丙啶开环反应，以生成氟化二氨基酸衍生物。基于氟选择性开环氮丙啶的方法已得到推广，可用于制备单环或双环氟化物质。
