Innovative Drug Research Centre (IDRC), School of Pharmaceutical Sciences, Chongqing University , Chongqing 401331, China.
Department of Chemistry, Sungkyunkwan University , Suwon 440-746, Korea.
Org Lett. 2017 May 5;19(9):2298-2301. doi: 10.1021/acs.orglett.7b00813. Epub 2017 Apr 25.
A chiral fluoride-catalyzed asymmetric cascade sulfa-Michael/aldol condensation reaction of 1,4-dithiane-2,5-diol and a series of α,β-unsaturated ketones is described to access chiral trisubstituted tetrahydrothiophene derivatives. The target products, including the spiro tetrahydrothiophene derivatives bearing a five-, six-, and seven-membered ring, were highly functionalized and showed high ee value. This established protocol realized a highly enantioselective reaction with a catalytic amount of KF and Song's chiral oligoEG via in situ generated chiral fluoride to construct useful heterocyclic skeletons with great complexity.
一种手性氟化物催化的不对称级联亚砜迈克尔/醛缩合反应，涉及 1,4-二硫杂环戊烷-2,5-二醇和一系列α,β-不饱和酮，用于获得手性三取代四氢噻吩衍生物。目标产物包括带有五、六和七元环的螺四氢噻吩衍生物，具有高度官能化和高ee 值。该方法通过原位生成的手性氟化物，使用催化量的 KF 和 Song 的手性寡聚 EG，实现了高对映选择性反应，构建了具有高度复杂性的有用杂环骨架。
