Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 11, Pages 1540-1546Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601645
Keywords
Synthetic methods; Mannich reaction; Fluorine; Imines; Diastereoselectivity
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Funding
- National Natural Science Foundation of China [21102071, 21472082]
- Jiangsu 333 program
- IKERBASQUE
- Basque Foundation for Science
- Changzhou Jin-Feng-Huang program
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Reported herein is a design and synthesis of N-tertbutylsulfinyl-( 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 beta-perfluorophen-yl-beta-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.
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