Asymmetric Synthesis of Quaternary β‐Perfluorophenyl‐β‐amino‐indolin‐2‐ones. Issue 11 (23rd March 2017)

• Record Type: Journal Article
• Authors: Zhang, Wenzhong; Sha, Wanxing; Zhu, Yi; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi
• Is Part Of: European journal of organic chemistry. Issue 11(2017)
• Page Start: 1540
• Page End: 1546
• Publication Date: 2017-03-23
• Subjects: Synthetic methods -- Mannich reaction -- Fluorine -- Imines -- Diastereoselectivity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601645
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Reported herein is a design and synthesis of N ‐ tert ‐butylsulfinyl‐(perfluoro)benzaldimine, and a study of its reactivity and stereocontrolling properties in Mannich addition reactions with indolinone derived tertiary enolates generated in situ. The corresponding products, quaternary β‐perfluorophenyl‐β‐amino‐indolin‐2‐ones, were obtained with good to excellent yields and diastereoselectivity, underscoring the exciting synthetic potential of this newly introduced pentafluorophenyl‐containing chiral imine. Abstract : A new chiral imine, N ‐ tert ‐butylsulfinyl‐(perfluoro)benzaldimine, has been developed and studied as a reagent in Mannich addition reactions with indolinone‐derived tertiary enolates generated in situ. The reaction proceeds smoothly to give the corresponding quaternary β‐perfluorophenyl‐β‐amino‐indolin‐2‐ones, with good to excellent yields and diastereoselectivities.