Organic Letters
Organic Letters
5 years ago

Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines

Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
Lin Peng, Feng Chen, Xiang-Jia Song, Li-Xin Wang, Hong-Xia Ren, Fang Tian, Yu Yang, Zheng-Bing Zhang, Chao Chen, Ying Zou
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00893

DOI: 10.1021/acs.orglett.7b00893

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