N-叔丁基亚磺酰基异氰酸酯的非对映选择性α-氟化反应。
Diastereoselective α-Fluorination of N- tert-Butanesulfinyl Imidates.
机构信息
Key Laboratory of Plant Resources and Chemistry of Arid Zones, Xinjiang Technical Institute of Physics and Chemistry , Chinese Academy of Sciences , Urumqi 830011 , China.
School of Chemical Science and Technology , Yunnan University , Kunming 650091 , China.
出版信息
J Org Chem. 2018 Dec 7;83(23):14777-14785. doi: 10.1021/acs.joc.8b02375. Epub 2018 Nov 8.
A diastereoselective α-fluorination of N- tert-butanesulfinyl imidates was developed. Deprotonation of N- tert-butanesulfinyl imidates with lithium hexamethyldisilazide generates aza-enolates that can be intercepted, with excellent diastereocontrol, by the inexpensive electrophilic fluorinating agent NFSI. This protocol was applied to the preparation of synthetically useful trans-2-fluoro-cyclohexamine with high enantiomeric purity (99.5% ee).
我们开发了一种 N-叔丁基亚磺酰基异氰酸酯的非对映选择性α-氟化方法。用六甲基二硅氮锂将 N-叔丁基亚磺酰基异氰酸酯脱质子，生成氮杂烯醇盐，它可以与廉价的亲电氟化试剂 NFSI 很好地进行立体选择性捕获。该方法被应用于具有高对映体纯度（99.5%ee）的合成有用的反式-2-氟环己胺的制备。
Zotero 插件