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Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

ABSTRACT: A convenient copper-catalyzed intramolecular/intermolecular alkene diamination reaction to synthesize 3-aminomethyl-functionalized isoxazolidines under mild reaction conditions and with generally high levels of diastereoselectivity was achieved. This reaction demonstrates that previously underutilized unsaturated carbamates are good [Cu]-catalyzed diamination substrates. Sulfonamides, anilines, benzamide, morpholine, and piperidine can serve as the external amine source. This relatively broad amine range is attributed to the mild reaction conditions. Reduction of the N-O bond could also be achieved, revealing the corresponding 3,4-diamino-1-alcohols efficiently.

SUBMITTER: Khoder ZM

PROVIDER: S-EPMC5944859 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.

Khoder Zainab M ZM Wong Christina E CE Chemler Sherry R SR

ACS catalysis 20170615 7

A convenient copper-catalyzed intramolecular/intermolecular alkene diamination reaction to synthesize 3-aminomethyl-functionalized isoxazolidines under mild reaction conditions and with generally high levels of diastereoselectivity was achieved. This reaction demonstrates that previously underutilized unsaturated carbamates are good [Cu]-catalyzed diamination substrates. Sulfonamides, anilines, benzamide, morpholine, and piperidine can serve as the external amine source. This relatively broad am ...[more]

PMID: 29755827

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