Direct Synthesis of N-Acyl-N,O-hemia cetals via Nucleophilic Addition of Unactivated Amides and Their O-Acetylation: Access to alpha , alpha -Difunctionalized N-Acylimines

A mild, metal-free synthesis of polyfunctionalized N-acyl-N,O-hemia cetals was developed via the nucleophilic addition of unactivated amides to ketones. The protocol demonstrated a wide substrate scope, with good isolated yields. Additionally, their O-acetylated products serve as a precursor of alph...

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Veröffentlicht in:	Advanced synthesis & catalysis 2016-09, Vol.358 (17), p.2817-2828
Hauptverfasser:	Asahara, Haruyasu, Inoue, Kanami, Tani, Shinki, Umezu, Kazuto, Nishiwaki, Nagatoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	Amides Catalysis Ketones Nucleophiles Precursors Substrates Synthesis
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creator	Asahara, Haruyasu Inoue, Kanami Tani, Shinki Umezu, Kazuto Nishiwaki, Nagatoshi
description	A mild, metal-free synthesis of polyfunctionalized N-acyl-N,O-hemia cetals was developed via the nucleophilic addition of unactivated amides to ketones. The protocol demonstrated a wide substrate scope, with good isolated yields. Additionally, their O-acetylated products serve as a precursor of alpha , alpha -difunctionalized N-acylimines. An addition reaction of broad scope of nucleophiles to generate N-acylimines is also reported.
doi_str_mv	10.1002/adsc.201600436
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subjects	Amides Catalysis Ketones Nucleophiles Precursors Substrates Synthesis
title	Direct Synthesis of N-Acyl-N,O-hemia cetals via Nucleophilic Addition of Unactivated Amides and Their O-Acetylation: Access to alpha , alpha -Difunctionalized N-Acylimines
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