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Asymmetric Synthesis of Quaternary β‐Perfluorophenyl‐β‐amino‐indolin‐2‐ones
Author(s) -
Zhang Wenzhong,
Sha Wanxing,
Zhu Yi,
Han Jianlin,
Soloshonok Vadim A.,
Pan Yi
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601645
Subject(s) - chemistry , imine , reactivity (psychology) , combinatorial chemistry , enantioselective synthesis , quaternary , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , paleontology , biology
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.