Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
University of Chinese Academy of Sciences , Beijing 100049, China.
Org Lett. 2017 Jun 2;19(11):2805-2808. doi: 10.1021/acs.orglett.7b00893. Epub 2017 May 12.
An unusual and highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and excellent stereoselectivities (up to >99:1 dr and >99% ee). The efficiency and potentials of the new reaction and the target chiral entities were well demonstrated by delicate transformations into a series of new chiral indolines.
一种由手性双功能胺螺二酰胺催化的硝基芳族化合物与羟马来酰亚胺的不寻常且高效的不对称环化反应已经被揭示。通过这种方法，可以直接有效地制备具有两个连续的季立体中心和多功能基团的广泛的高度稠合的手性 N-羟基吲哚啉，产率优异（高达＞99%），区域选择性环化和立体选择性优异（高达＞99:1 dr 和＞99%ee）。通过一系列新的手性吲哚啉的精细转化，充分证明了新反应和目标手性实体的效率和潜力。
