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Divergent Reactivity of gem-Difluoro-enolates toward Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of α-Ketoamides

Mallu Kesava Reddy, Isai Ramakrishna, Mahiuddin Baidya*

*Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamil Nadu, India, Email: mbaidyaiitm.ac.in

M. K. Reddy, I. Ramakrishna, M. Baidya, Org. Lett., 2018, 20, 4579-4583.

DOI: 10.1021/acs.orglett.8b01900 (free Supporting Information)



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Abstract

An amination reaction of in situ generated gem-difluoro-enolates with nitrosoarenes furnished α-ketoamides in very high yields. This nitroso aldol reaction is very fast (typically completed within 5 min) and scalable and tolerates various sensitive functional groups. Amination with azodicarboxylates smoothly produced fluorinated α-amino ketones.

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Key Words

α-keto amides, amination


ID: J54-Y2018